Optically active compound, liquid crystal composition containing the same, liquid crystal device using the same, liquid crystal apparatus and display method

ABSTRACT

An optically active compound represented by the formula R 1  --A 1  --A 2  --X 1  --A 3  --(CH 2 ) p  --L--A 4  --R 2 , in which R 1  is F, CN or straight chain, branched or cyclic alkyl and R 2  is H, F, CH or straight chain or branched alkyl; A 3  is 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, pyridazine-3,6-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-ditiane-2,5-diyl, thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzoxazole-2,5-diyl, benzoxazole-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, quinoxaline-2,6-diyl, quinoline-2,6-diyl, 2,6-naphthylene, indane-2,5-diyl, 2-alkylindane-2,5-diyl, indanone-2,6-diyl, 2-alkylindane-2,6-diyl, coumarane-2,5-diyl and 2-alkylcoumarane-2,5-diyl; A 1 , A 2  and A 4  are single bond or A 3  ; X 1  &#39; is a single bond, --COO--, --OCO--, --CH 2  O--, --OCH 2  --, --CH 2  CH 2  --, --CH═CH-- or --C.tbd.C--; p is an integer from 2 to 20; and L is optically active.

This application is a continuation of application Ser. No. 08/371,854,filed Jan. 12, 1995, now abandoned.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a novel optically active compound, aliquid crystal composition containing the same, a liquid crystal deviceusing the same and a liquid crystal apparatus. More particularly, thepresent invention relates, to a novel liquid crystal composition havingan improved response characteristic with respect to an electric field, aliquid crystal display device using the same, a liquid crystal devicefor use in a liquid crystal-optical shutter and a display apparatususing the liquid crystal device to display information.

2. Related Background Art

Hitherto, liquid crystal has been used in a variety of industrial fieldsas an electro-optical device. A major portion of liquid crystal devicesuses a TN (Twisted Nematic) type liquid crystal disclosed in, forexample, "Voltage Dependent Optical Activity of a Twisted Nematic LiquidCrystal", M. Schadt and W. Helfrich, P.127 and P.128, Vol. 18, No. 4(Feb. 15, 1971) of "Applied Physics Letters". The TN liquid crystaldevices act on the basis of the dielectric arrangement effect of theliquid crystal, the effect being realized by the dielectric anisotropyof liquid crystal molecules such that the direction of the averagemolecular axis is oriented into a specific direction by the electricfield. It has been said that the optical response speed of the TN liquidcrystal devices is limited to milliseconds, the speed beingunsatisfactory for a multiplicity of applications.

In view of application to a large size and plane display, operationusing a simple matrix method is a most advantageous method to reduce thecost and realize a satisfactory manufacturing yield. The simple matrixmethod employs an electrode structure formed such that a scanningelectrode group and a signal electrode group are arranged into a matrixconfiguration. To operate an electrode structure of the foregoing type,a time division operation method has been employed in which addresssignals are selectively, sequentially and periodically applied to thescanning electrode group; and predetermined information signals areselectively and in parallel applied to the signal electrode group insynchronization with the address signals.

However, employment of the TN type liquid crystal in the device operatedby the foregoing method results in finite application of an electricfield to a region (a so-called "semi-selected point") in which ascanning electrode is selected and as well as no signal electrode isselected or a region in which no scanning electrode is selected and aswell as a signal electrode is selected. If the difference betweenvoltage applied to the selected point and that applied to thesemi-selected point is sufficiently large and if a voltage thresholdrequired to orient liquid crystal molecules perpendicular to theelectric field is set to an intermediate voltage between the foregoingvoltages, the display device can be operated normally. If the number (N)of the scanning lines is increased, time (the duty ratio), in which aneffective electric field is applied to one selected point, is shortenedundesirably at a rate of 1/N during scanning the overall screen (oneframe). Therefore, the difference between effective voltagesrespectively applied to the selected point and the non-selected point isreduced in inverse proportion to the number of the scanning lines. As aresult, the contrast of the image is undesirably lowered and a problemof cross talk cannot be overcome.

The foregoing phenomenon takes place when liquid crystal having nobistability (the "stable state" is a state where liquid crystalmolecules are oriented horizontally with respect to the surface of theelectrode and liquid crystal molecules are oriented vertically only whenthe electric field is effectively applied) is operated by using a timeaccumulation effect (that is, scanned repeatedly). Therefore, theforegoing problem is an inherent problem that cannot be overcome.

To overcome the foregoing problem, a voltage averaging method, atwo-frequency operation method and a multi-matrix method have beensuggested, resulting in that a satisfactory effect has not beenobtained. Therefore, any of the foregoing methods has beenunsatisfactory and trends for enlarging the screen formed by the displaydevices and for raising the density have encountered limitations.

To overcome the problems experienced with the conventional liquidcrystal device, use of a liquid crystal device having bistability hasbeen suggested by Clark and Lagerwall (see Japanese Patent Laid-Open No.56-107216 and U.S. Pat. No. 4,367,924).

As the bistable liquid crystal, ferroelectric liquid crystal havingchiral smectic phase C (phase S*C) or phase H (phase S*H) is usuallyused. The ferroelectric liquid crystal has bistability with respect toan electric field, the bistability being consisting of a first opticallystable state and a second optically stable state. Therefore, unlike theoptically modulating devices for use in the foregoing conventional TNtype liquid crystal, liquid crystal molecules are oriented in the firstoptically stable state with respect to either electric field vector andliquid crystal molecules are oriented in the second optically stablestate with respect to another electric field. Furthermore, liquidcrystal of the foregoing type has characteristics (bistability) ofhaving either of the two stable states in response to the added electricfield and as well as maintaining the foregoing state if no electricfield is added.

The ferroelectric liquid crystal has an excellent characteristic of ahigh speed response as well as the bistability. The reason for this isthat the spontaneous polarization of the ferroelectric liquid crystaland the applied electric field directly react with each other to inducetransition of the state of orientation. As a result, the response speedis, by 3 to 4 orders, higher than that realized due to the reactionbetween the dielectric anisotropy and the electric field.

Since the ferroelectric liquid crystal latently has the excellentcharacteristics as described above, use of the characteristics enablesthe foregoing problems experienced with the conventional TN type deviceto be overcome substantially essentially. Therefore, applying of theferroelectric liquid crystal to a high speed optical shutter and ahigh-density and large-size display is expected. Hence, liquid crystalmaterials having the ferroelectric characteristic have been widelystudied. However, the ferroelectric liquid crystal materials, that havebeen developed, are unsatisfactory in terms of their characteristicsrequired for the liquid crystal device including the operationality atlow temperatures, high speed response and contrast.

In the ferroelectric liquid crystal, response time τ, the intensity Psof the spontaneous polarization and the viscosity η have the followingrelationship represented by the following equation (1): ##EQU1## where Eis an applied electric field.

Therefore, the response speed can be raised by any of the followingmethods:

(a) The intensity of the spontaneous polarization is raised.

(b) The viscosity η is reduced.

(c) The applied electric field E is enlarged.

However, the upper limit of the applied electric field is presentbecause the ferroelectric liquid crystal is operated by an IC or thelike. Therefore, it is preferable that the applied electric field isminimized. As a result, the viscosity η must be reduced or the intensityPs of the spontaneous polarization must be enlarged. In general,ferroelectric chiral smectic liquid crystal compound having a largespontaneous polarization involves a trend of having a large internalelectric field generated by the spontaneous polarization and thereforeencounters a great limitation in allowable device structures which arecapable of realizing the bistable state. If the spontaneous polarizationis enlarged excessively, the viscosity is also raised, thus resulting inthat the response speed cannot be raised as desired.

In a case where the actual temperature range for the display is about 5°C. to about 40° C., the response speed usually changes about 20 timeswhich exceed the limit adjustable by changing the operation voltage andthe frequency.

The liquid crystal device adapted to use the refractivity of liquidcrystal usually has a transmissivity under a crossed-Nicol representedby the following equation (2): ##EQU2## where I₀ is intensity ofincidental light, I is intensity of transmissive light, θ_(a) is anapparent tilt angle defined later, Δn is anisotropy of the refractivity,d is the thickness of a liquid crystal layer and λ is the wavelength ofincidental light. The tilt angle θ_(a) in the foregoing non-spiralstructure is caused to appear as the angle of the direction of theaverage molecule axis of liquid crystal molecules twisted in the firstand second states of orientation. According to equation (2), when theapparent tilt angle θ_(a) is 22.5°, the maximum transmissivity is madehighest. Therefore, the apparent tilt angle θ_(a) in the non-spiralstructure for realizing the bistability must be closer to 22.5°.

However, application to the non-spiral ferroelectric liquid crystaldisclosed by Clark and Lagerwall and having bistability raises thefollowing problems that undesirably lower the contrast.

First, since the tilt angle θ_(a) (the half of an angle made by axes ofmolecules in the two stable states) in the conventional non-spiralferroelectric liquid crystal formed by an orienting process using apolyimide film subjected to a rubbing process is smaller than the tiltangle (angle θ which is the half of the apex angle of a triangular prismto be described later) of the ferroelectric liquid crystal, thetransmissivity is low. Second, although the contrast can be raised in astatic state in which no electric field is applied, black images areundesirably lightened because liquid crystal molecules are fluctuated bya small electric field during the non-selected period in the matrixoperation in a case where an image is displayed by applying a voltage.

As described above, to realize the ferroelectric liquid crystal device,a liquid crystal composition having a chiral smectic phase is required,which exhibits high speed response, the response speed of which does notconsiderably depend on temperatures and which has high contrast.Furthermore, uniform switching of the display, excellent visual anglecharacteristic, low temperature dependency and reduction of loads on theoperating IC must be realized by making adequate the spontaneouspolarization, chiral smectic pitch C, cholesteric pitch, temperaturerange, in which the liquid phase is realized, the optical anisotropy,tilt angle and the dielectric anisotropy.

SUMMARY OF THE INVENTION

Accordingly, an object of the present invention is to provide anoptically active compound capable of attaining a large spontaneouspolarization, having high speed response, capable of reducing thetemperature dependency of the response speed and realizing high contrastso as to put into practice a chiral smectic liquid crystal device, inparticular, a ferroelectric liquid crystal liquid crystal device, andalso to a liquid crystal composition containing the same, in particulara chiral smectic liquid crystal composition, a liquid crystal apparatus,and a display method which uses the foregoing liquid crystalcomposition.

According to the present invention, there is provided an opticallyactive compound comprising a structure represented by the followinggeneral formula (I):

    R.sub.1 --A.sub.1 --A.sub.2 --X.sub.1 --A.sub.3 --(CH.sub.2).sub.p --L--A.sub.4 --R.sub.2                                    (I)

where R₁ and R₂ respectively are H, F, CN or straight chain, branched orcyclic alkyl group (one or more --CH₂ -- in the alkyl group may bereplaced by --O--, --S--, --CO--, --CH (CN)--, --CH═CH-- or --C.tbd.C--under condition that hetero atoms do not position adjacent and thehydrogen atom in the alkyl group may be replaced by a fluorine atom)having 1 to 30 carbon atoms, A₃ is a group selected from the groupconsisting of 1, 4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl,pyrazine-2,5-diyl, pyridazine-3,6-diyl, 1,4-cyclohexylene,1,3-dioxane-2,5-diyl, 1,3-ditiane-2,5-diyl, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzoxazole-2,5-diyl,benzoxazole-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl,benzofuran-2,5-diyl, benzofuran-2,6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene, indane-2,5-diyl,2-alkylindane-2,5-diyl (the alkyl group is a straight chain or branchedalkyl group having 1 to 18 carbon atoms), indanone-2,6-diyl,2-alkylindane-2,6-diyl (the alkyl group is a straight chain or branchedalkyl group having 1 to 18 carbon atoms), coumarane-2,5-diyl and2-alkylcoumarane-2,5-diyl (the alkyl group is a straight chain orbranched alkyl group having 1 to 18 carbon atoms), each of which may besubstituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN, A₁, A₂ and A₄ are single bondsor selected from A₃, X₁ is a single bond, --COO--, --OCO--, --CH₂ O--,--OCH₂ --, --CH₂ CH₂ --, --CH═CH-- or --C.tbd.C--, p is an integer from2 to 20, L is optically active butanolyde-2,4-diyl or optically active4-alkylbutanolyde-2,4-diyl (the alkyl group is straight-chain orbranched alkyl group having 1 to 5 carbon atoms) or optically active2-alkylbutanolyde-2,4-diyl (the alkyl group is straight-chain orbranched alkyl group having 1 to 5 carbon atoms).

According to another aspect of the present invention, there is provideda liquid crystal composition containing one or more kinds of theoptically active compounds as an essential component.

According to further aspect of the present invention, there are provideda liquid crystal device having the foregoing liquid crystal compositiondisposed between a pair of electrode substrates, a liquid crystalapparatus having the liquid crystal device, in particular, a displayapparatus, and a display method for displaying information bycontrolling the foregoing liquid crystal composition.

Other and further objects, features and advantages of the invention willbe evident from the following detailed description of the preferredembodiments in conjunction with the attached drawings.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a schematic cross sectional view which illustrates an exampleof a liquid crystal device using liquid crystal having a chiral smecticphase according to the present invention;

FIG. 2 is a perspective view which schematically illustrates an exampleof a device cell to explain the operation of a liquid crystal deviceusing ferroelectric characteristic of liquid crystal;

FIG. 3 is a perspective view which schematically illustrates an exampleof the structure of a device cell to explain the operation of a liquidcrystal device using the ferroelectric characteristic of liquid crystal;

FIG. 4 illustrates tilt angle (θ) of a liquid crystal molecule;

FIGS. 5(A) and 5(B) show waveforms in a method of operating the liquidcrystal device according to the present invention;

FIG. 6 is a schematic view which illustrates a display pattern to beperformed when an actual operation is performed with the time sequentialoperation waveforms shown in FIG. 5;

FIG. 7 is a block diagram which illustrates a liquid crystal displayapparatus having a chiral smectic liquid crystal device according to thepresent invention and a graphic controller; and

FIG. 8 is a timing chart of image information communication between theliquid crystal display apparatus and the graphic controller.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

Preferred embodiments of the present invention will now be described.

In an optically active compound according to the present invention andrepresented by chemical formula (I), R₁, R₂, A₁, A₂, A₃, A₄, X₁, L and pmay be combined within the aforesaid range. Although preferredcombinations will be described, individual combinations of the describedmaterials are suitably selected.

Among the optically active compounds represented by general formula (I),a compound satisfying any of requirements (Ia) to (Id) is preferablyexemplified in the view points of the temperature range for the liquidcrystal phase, miscibility, viscosity and orienting characteristic. (Ia)An optically active compound in which A₁ and A₂ are respectively singlebonds or a group selected from the group consisting of 1,4-phenylene,pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyrazine-2,5-diyl,pyridazine-3,6-diyl, 1,4-cyclohexylene, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzoxazole-2,5-diyl,benzoxazole-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl,benzofuran-2,5-diyl, benzofuran-2-6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene, indane-2,5-diyl andcoumarane-2,5-diyl, each of which may be substituted by at least onesubstituent selected from the group consisting of F, Cl, Br, CH₃, CF₃and CN, A₃ is 1,4-phenylene, which may be substituted by one or moresubstituent selected from a group consisting of F, Cl, Br, CH₃, CF₃ orCN and A₄ is a single bond.

(Ib) An optically active compound in which A₁ and A₂ are respectivelysingle bonds or 1,4-phenylene, which may be substituted by at least onesubstituent selected from the group consisting of F, Cl, Br, CH₃, CF₃and CN, A₃ is a material selected from a group consisting ofpyridine-2,5-diyl, pyrimidine-2,5-diyl, pyrazine-2,5-diyl,pyridazine-3,6-diyl, 1,4-cyclohexylene, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzoxazole-2,5-diyl,benzoxazole-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl,benzofuran-2,5-diyl, benzofuran-2-6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene, indane-2,5-diyl orcoumarane-2,5-diyl and A₄ is a single bond.

(Ic) An optically active compound in which A₁ is a single bond, A₂ andA₄ are respectively groups selected from the group consisting of1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl,pyrazine-2,5-diyl, pyridazine-3,6-diyl, 1,4-cyclohexylene,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,benzoxazole-2,5-diyl, benzoxazole-2,6-diyl, benzothiazole-2,5-diyl,benzothiazole-2,6-diyl, benzofuran-2,5-diyl, benzofuran-2-6-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl, 2,6-naphthylene,indane-2,5-diyl and coumarane-2,5-diyl, each of which may be substitutedby at least one substituent selected from the group consisting of F, Cl,Br, CH₃, CF₃ and CN, and A₃ is 1,4-phenylene, which may be substitutedby at least one substituent selected from the group consisting of F, Cl,Br, CH₃, CF₃ and CN.

(Id) An optically active compound in which A₁ is a single bond, A₂ is asingle bond or 1,4-phenylene, which may be substituted by at least onesubstituent selected from the group consisting of F, Cl, Br, CH₃, CF₃and CN, A₃ is a group selected from the group consisting ofpyridine-2,5-diyl, pyrimidine-2,5-diyl, pyrazine-2,5-diyl,pyridazine-3,6-diyl, 1,4-cyclohexylene, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzoxazole-2,5-diyl,benzoxazole-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl,benzofuran-2,5-diyl, benzofuran-2-6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene, indane-2,5-diyl andcoumarane-2,5-diyl and A₄ is 1,4-phenylene, each of which may besubstituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN.

Further preferred compounds are the following compounds that satisfy anyof the following requirements (Iaa to Idb):

(Iaa) An optically active compound in which A₁, A₂, A₄ and X₁ arerespectively single bonds, and A₃ is 1,4-phenylene, which may besubstituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN.

(Iab) An optically active compound in which A₁, A₄ and X₁ are singlebonds, A₂ is a group selected from the group consisting of1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl,1,4-cyclohexylene, thiophene-2,5-diyl, thiazole-2,5-diyl,thiaziazole-2,5-diyl, benzothiazole-2,6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene and indane-2,5-diyl, each of whichmay be substituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN, and A₃ is 1,4-phenylene, whichmay be substituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN.

(Iac) An optically active compound in which A₄ and X₁ are single bonds,A₁ is pyrimidine-2,5-diyl, A₂ and A₃ are 1,4-phenylene, which may besubstituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN.

(Iad) An optically active compound in which A₄ and X₁ are single bonds,A₁ and A₂ are groups selected from the group consisting of1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl,1,4-cyclohexylene, thiophene-2,5-diyl, thiazole-2,5-diyl,thiaziazole-2,5-diyl and indane-2,5-diyl, each of which may besubstituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN, and A₃ is 1,4-phenylene, whichmay be substituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN.

(Iba) An optically active compound in which A₁, A₂, A₄ and X₁ are singlebonds, A₃ is a group selected from the group consisting ofpyridine-2,5-diyl, 1,4-cyclohexylene, quinoxaline-2,6-diyl,quinoline-2,6-diyl and 2,6-naphthylene.

(Ibb) An optically active compound in which A₁, A₄ and X₁ are singlebonds, A₂ is 1,4-phenylene, which may be substituted by at least onesubstituent selected from the group consisting of F, Cl, Br, CH₃, CF₃and CN, and A₃ is a group selected from the group consisting ofpyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,4-cyclohexylene,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl and 2,6-naphthylene.

(Ica) An optically active compound in which A₁ and X₁ are single bonds,A₂ is a group selected from the group consisting of 1,4-phenylene,pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,4-cyclohexylene,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,benzothiazole-2,6-diyl, quinoxaline-2,6-diyl, quinoline-2,6-diyl,2,6-naphthylene and indane-2,5-diyl, each of which may be substituted byat least one substituent selected from the group consisting of F, Cl,Br, CH₃, CF₃ and CN, and A₃ and A₄ 1,4-phenylene, which may besubstituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN.

(Ida) An optically active compound in which A₁ and X₁ are single bonds,A₃ is a group selected from the group consisting of pyridine-2,5-diyl,pyrimidine-2,5-diyl, 1,4-cyclohexylene, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzothiazole-2,6-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl, 2,6-naphthylene andindane-2,5-diyl, A₂ and A₄ are 1,4-phenylene, which may be substitutedby at least one substituent selected from the group consisting of F, Cl,Br, CH₃, CF₃ and CN.

(Idb) An optically active compound in which A₁, A₂ and X₁ are singlebonds, A₃ is a group selected from the group consisting of1,4-phenylene, pyridine-2,5-diyl, 1,4-cyclohexylene,quinoxaline-2,6-diyl, quinoline-2,6-diyl and 2,6-naphthylene, which maybe substituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN, and A₄ is 1,4-phenylene, whichmay be substituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN.

In a case where 1,4-phenylene having one or two substituents (F, Cl, Br,CH₃, CF₃ or CN) is contained in the optically active compoundrepresented by general formula (I), preferred substituent is any of F,Cl, Br and CF₃, and more preferably F.

In the structure in general formula (I), L is usually optically active4-butanolyde-2,4-diyl or optically active 4-alkyl-4-butanolyde-2,4-diyl(the alkyl group is straight-chain or branched alkyl group having 1 to 5carbon atoms) or optically active 2-alkyl-4-butanolyde-2,4-diyl (thealkyl group is straight-chain or branched alkyl group having 1 to 5carbon atoms).

R₁ and R₂ are selected from (i) to (xvi). ##STR1## where a is an integerfrom 1 to 16, d, g and i are integers from 0 to 7, b, e, h, j and k areintegers from 1 to 10, f and w respectively are 0 or 1, m, n, q, r, sand t are integers from 0 and 10 in which b+d≦16, e+f+g≦16 and h+i≦16are satisfied, E is CH₃ or CF₃, Y₁ is a single bond, --O--, --COO-- or--OCO--, Y₂ is --COO--, --CH₂ O--, --CH₂ CH₂ O--, --CH₂ CH₂ CH₂ O-- or--CH₂ CH₂ --, Y₃ is a single bond, --COO--, --CH₂ O--O, --OCO-- or--OCH₂ which may be optically active materials, and p is preferably aninteger from 2 to 12, and further preferably an integer from 2 to 9.

The five-membered cyclic lacton-based compound serving as the opticallyactive compound and a liquid crystal composition containing the samehave been disclosed in Japanese Patent Laid-Open No. 2-138274, JapanesePatent Laid-Open No. 2-138385 (U.S. Pat. No. 4,973,425), Japanese PatentLaid-Open No. 2-261893, Japanese Patent Laid-Open No. 2-286673, JapanesePatent Laid-Open No. 2-289561, Japanese Patent Laid-Open No. 3-52882,Japanese Patent Laid-Open No. 3-58981, Japanese Patent Laid-Open No.3-173878, Japanese Patent Laid-Open No. 3-173879, Japanese PatentLaid-Open No. 4-193872 and Japanese Patent Laid-Open No. 4-334376.However, the foregoing compounds have a structure that the linkingportion of the lactone ring and that of the mesogen skeleton are bondedwith a methyleneoxy group or a single bond and no disclosure has beenmade about the compound according to the present invention in which thelactone ring is bonded by an alkylene bond. Furthermore, no descriptionhas been made about the characteristics and effects of the compoundaccording to the present invention. According to the present invention,there is provided a novel optically active five-membered cyclic lactonecompound characterized in that the lactone ring and the mesogen skeletonare bonded with each other by the alkylene bond which is flexible andattains low viscosity. The present invention is structured based on aknowledge that the foregoing compound is capable of attaining a largespontaneous polarization, having high speed response, capable ofreducing the temperature dependency of the response speed and realizinghigh contrast.

As the optically active compound represented by general formula (I), itis particularly preferable that a compound specifically represented bythe following general formula (I') is employed: ##STR2## where R₁ ' isH, F, CN or a straight, branched or cyclic alkyl group (one or more--CH₂ -- in the alkyl group may he replaced by --O--, --S--, --CO--,--CH (CN)--, --CH═CH-- or --C.tbd.C-- under condition that hetero atomsdo not position adjacent and the hydrogen atom in the alkyl group may bereplaced by a fluorine atom) having 1 to 20 carbon atoms, R₂ ' is astraight or branched alkyl group (one or more --CH₂ -- in the alkylgroup may be replaced by --O--, --CO-- or --CH═CH-- under condition thathetero atoms do not position adjacent and the hydrogen atom in the alkylgroup may be replaced by a fluorine atom), A₃ ' is a group selected fromthe group consisting of 1,4-phenylene, pyridine-2,5-diyl,pyrimidine-2,5-diyl, pyrazine-2,5-diyl, pyridazine-3,6-diyl,1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-ditiane-2,5-diyl,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,benzoxazole-2,5-diyl, benzoxazole-2,6-diyl, benzothiazole-2,5-diyl,benzothiazole-2,6-diyl, benzofuran-2,5-diyl, benzofuran-2-6-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl, 2,6-naphthylene,indane-2,5-diyl, alkylindane-2,5-diyl (the alkyl group is a straightchain or branched alkyl group having 1 to 18 carbon atoms),indanone-2,6-diyl, 2-alkylindane-2,6-diyl (the alkyl group is a straightchain or branched alkyl group having 1 to 18 carbon atoms),coumarane-2,5-diyl and 2-alkylcoumarane-2,5-diyl (the alkyl group is astraight chain or branched alkyl group having 1 to 18 carbon atoms),each of which may be substituted by at least one substituent selectedfrom the group consisting of F, Cl, Br, CH₃, CF₃ and CN, A₁ ' and A₂ 'are respectively single bonds or selected from A₃ ', X₁ ' is a singlebond, --COO--, --OCO--, --CH₂ O--, --OCH₂ --, --CH₂ CH₂ --, --CH═CH-- or--C.tbd.C--, and * represents optically active characteristic.

Among the optically active compounds represented by general formula(I'), it is preferable to employ a compound satisfying the followingcondition (Ia') or (Ib') in viewpoints of the temperature range for theliquid crystal phase, the mixing easiness, the viscosity and orientingeasiness for the liquid crystal:

(Ia') An optically active compound in which A₁ ' and A₂ ' are singlebonds or groups selected from the group consisting of 1,4-phenylene,pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyrazine-2,5-diyl,pyridazine-3,6-diyl, 1,4-cyclohexylene, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzoxazole-2,5-diyl,benzoxazole-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl,benzofuran-2,5-diyl, benzofuran-2-6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene, indane-2,5-diyl andcoumarane-2,5-diyl, each of which may be substituted by at least onesubstituent selected from the group consisting of F, Cl, Br, CH₃, CF₃and CN and A₃ is 1,4-phenylene, which may be substituted by at least onesubstituent selected from the group consisting of F, Cl, Br, CH₃, CF₃and CN and A₄ is a single bond.

(Ib') An optically active compound in which A₁ ' and A₂ ' are singlebonds or 1,4-phenylene, which may be substituted by at least onesubstituent selected from the group consisting of F, Cl, Br, CH₃, CF₃and CN, A₃ ' is a group selected from the group consisting ofpyridine-2,5-diyl, pyrimidine-2,5-diyl, pyrazine-2,5-diyl,pyridazine-3,6-diyl, 1,4-cyclohexylene, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzoxazole-2,5-diyl,benzoxazole-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl,benzofuran-2,5-diyl, benzofuran-2-6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene, indane-2,5-diyl andcoumarane-2,5-diyl.

As the optically active compound represented by general formula (I'), itis preferable that any material represented by (Iaa') to (Ibb') beemployed.

(Iaa') An optically active compound in which A₁ ', A₂ ' and X₁ ' aresingle bonds and A₃ ' is 1,4-phenylene, which may be at least onesubstituent selected from the group consisting of F, Cl, Br, CH₃, CF₃and CN.

(Iab') An optically active compound in which A₁ ' is a single bond andboth of A₂ ' and A₃ ' are 1,4-phenylene, which may be at least onesubstituent selected from the group consisting of F, Cl, Br, CH₃, CF₃and CN.

(Iac') An optically active compound in which A₁ ' and X₁ ' are singlebonds, A₂ ' is a group selected from the group consisting ofpyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,4-cyclohexylene,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,benzothiazole-2,6-diyl, quinoxaline-2,6-diyl, quinoline-2,6-diyl,2,6-naphthylene and indane-2,5-diyl, A₃ ' is 1,4-phenylene, which may besubstituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN.

(Iba') An optically active compound in which A₁ ', A₂ ' and X₁ ' aresingle bonds and A₃ ' is a group selected from the group consisting ofpyridine-2,5-diyl, 1,4-cyclohexylene, quinoxaline-2,6-diyl,quinoline-2,6-diyl and 2,6-naphthylene.

(Ibb') An optically active compound in which A₁ ' and X₁ ' are singlebonds, A₂ ' is 1,4-phenylene, which may be substituted by at least onesubstituent selected from the group consisting of F, Cl, Br, CH₃, CF₃and CN and A₃ ' is a group selected from the group consisting ofpyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,4-cyclohexylene,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl and 2,6-naphthylene.

In the optically active compound represented by general formula (I'), itis preferable that R₁ ' and R₂ ' are materials selected from a groupconsisting of (i') to (v'). ##STR3## where a' is an integer from 1 to16, d', g' and i' respectively are integers from 0 to 7, b', e', h' andj' respectively are integers from 1 to 10, f' is 0 or 1 in whichb'+d'≦16, e'+f'+g'≦16 and h'+i'≦16 are satisfied, Y1' is a single bond,--O--, --COO-- or --OCO-- and Y₂ ' is --COO-- or --CH₂ O--, which may beoptically active.

The optically active compound according to the present invention can beprepared by a method in which a lactone ring is formed in the finalstage thereof and which is exemplified by a method (A) having the stepsof converting an alcohol into tosyl so as to be prepared into a malonicacid derivative; and causing it to react with an optically activeoxirane and a method (B) having the steps of coupling oxirane having aolefin terminal with 9-BBN; and causing it to react with a derivative ofa malonic acid. The optically active compound can be prepared by formingthe lactone ring and by subjecting it to a coupling reaction(preparation examples (C) and (D)). ##STR4## where TsCl isp-toluenesulfonic acid chloride, and 9-BBN is 9-borabicyclo 3.3.1!nonaneand R₁, R₂, A₁, A₂, A₃, A₄, X₁ and P are the materials according to theforegoing general formula.

Schematic constitutional formulas of the optically active compound (thecompounds in general formula (I') included) represented by generalformula (I) are shown in Table 1. Hereinafter abbreviated formsrespectively represent the following groups. ##STR5##

                                      TABLE 1                                     __________________________________________________________________________    No.                                                                              R.sub.1     A.sub.1                                                                           A.sub.2                                                                           X.sub.1                                                                              A.sub.3                                                                           p  L  A.sub.4                                                                          R.sub.2                            __________________________________________________________________________     1 C.sub.6 H.sub.13                                                                          --  --  --     Ph  2  L1 -- C.sub.8 H.sub.17                    2 C.sub.8 H.sub.17 O                                                                        --  --  --     Ph  2  L1 -- C.sub.18 H.sub.37                   3 C.sub.5 H.sub.11 O                                                                        --  --  --     Ph2F                                                                              2  L1 -- C.sub.6 H.sub.13                    4 CH.sub.3 O  --  Ph  --     Ph  2  L1 -- C.sub.6 H.sub.13                    5 C.sub.6 H.sub.13 'CHF(CH.sub.2).sub.2 O                                                   --  Ph  --     Ph  2  L1 -- C.sub.6 H.sub.13                    6 C.sub.7 H.sub.15 O                                                                        --  Ph  --     Ph23F                                                                             2  L1 -- C.sub.6 H.sub.13                    7 C.sub.6 H.sub.13                                                                          --  Ph  --OCH.sub.2 --                                                                       Ph  2  L1 -- C.sub.9 H.sub.19                    8 C.sub.6 F.sub.13 CH.sub.2 O                                                               --  Ph  --C.tbd.C--                                                                          Ph  2  L1 -- C.sub.5 H.sub.11                    9 C.sub.8 H.sub.17 O                                                                        --  Ph  --COO--                                                                              Ph  2  L1 -- C.sub.6 H.sub.13                    10                                                                              C.sub.8 H.sub.17                                                                          --  Pr1 --     Ph  2  L1 -- C.sub.8 H.sub.17                    11                                                                              C.sub.10 H.sub.21                                                                         --  Pr2 --     Ph  2  L1 -- C.sub.4 H.sub.9                     12                                                                              C.sub.11 H.sub.23                                                                         --  Pr2 --     Ph  2  L1 -- C.sub.6 H.sub.13                    13                                                                              C.sub.12 H.sub.25                                                                         --  Pr2 --COO--                                                                              Ph  2  L1 -- C.sub.8 H.sub.17                    14                                                                              C.sub.4 H.sub.9 O                                                                         --  Py1 --     Ph  2  L1 -- C.sub.10 H.sub.21                   15                                                                              C.sub.13 H.sub.27                                                                         --  Py2 --     Ph  2  L1 -- C.sub.5 H.sub.11                    16                                                                              C.sub.6 H.sub.13 O                                                                        --  Py2 --     Ph  2  L1 -- C.sub.8 H.sub.17                    17                                                                              C.sub.6 H.sub.13 'CHFCH.sub.2 O                                                           --  Py2 --     Ph  2  L1 -- C.sub.9 H.sub.19                    18                                                                              C.sub.5 H.sub.11 O                                                                        --  Py2 --     Ph23F                                                                             2  L1 -- C.sub.4 H.sub.9                     19                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  2  L1 -- C.sub.6 H.sub.13                    20                                                                              C.sub.8 H.sub.17                                                                          --  Py2 --     Ph3F                                                                              2  L1 -- C.sub.7 H.sub.15                    21                                                                              C.sub.6 H.sub.13                                                                          --  Cy  --     Ph  2  L1 -- C.sub.4 H.sub.8 OC.sub.4                                                      H.sub.9                             22                                                                              C.sub.7 H.sub.15 OCO                                                                      --  Cy  --     Ph  2  L1 -- C.sub.14 H.sub.29                   23                                                                              C.sub.6 H.sub.13                                                                          --  Cy  --CH═CH--                                                                        Ph  2  L1 -- C.sub.10 H.sub.21                   24                                                                              C.sub.3 H.sub.7                                                                           --  Cy  --COO--                                                                              Ph  2  L1 -- C.sub.6 H.sub.13                    25                                                                              C.sub.5 H.sub.11                                                                          --  Pa  --     Ph  2  L1 -- C.sub.8 H.sub.17                    26                                                                              C.sub.10 H.sub.21                                                                         --  Pd  --     Ph  2  L1 -- C.sub.6 H.sub.13                    27                                                                              C.sub.6 H.sub.13                                                                          --  Dt2 --     Ph  2  L1 -- (CH.sub.2).sub.7 CH═CH.sub.                                               2                                   28                                                                              C.sub.8 H.sub.17                                                                          --  Tn  --     Ph  2  L1 -- C.sub.9 H.sub.19                    29                                                                              C.sub.6 H.sub.13 'CHFCH.sub.2 CH.sub.2                                                    --  Py2 --     Ph  2  L1 -- C.sub.6 H.sub.13                    30                                                                              C.sub.5 H.sub.11                                                                          --  Tz1 --     Ph  2  L1 -- C.sub.8 H.sub.17                    31                                                                              C.sub.9 H.sub.19 O                                                                        --  Tz2 --     Ph  2  L1 -- C.sub.5 H.sub.11                    32                                                                              C.sub.2 H.sub.5                                                                           --  Td  --     Ph  2  L1 -- C.sub.8 H.sub.17                    33                                                                              C.sub.10 H.sub.21                                                                         --  Dx2 --     Ph  2  L1 -- C.sub.7 H.sub.15                    34                                                                              C.sub.6 H.sub.13                                                                          --  Boa2                                                                              --     Ph  2  L1 -- C.sub.10 H.sub.21                   35                                                                              C.sub.7 H.sub.15                                                                          --  Bob2                                                                              --     Ph  2  L1 -- C.sub.6 H.sub.13                    36                                                                              C.sub.16 H.sub.33 O                                                                       --  Bta2                                                                              --     Ph  2  L1 -- C.sub.6 H.sub.13                    37                                                                              C.sub.6 H.sub.13                                                                          --  Btb2                                                                              --     Ph  2  L1 -- C.sub.14 H.sub.29                   38                                                                              C.sub.5 H.sub.11                                                                          --  Np  --COO--                                                                              Ph  2  L1 -- C.sub.7 H.sub.15                    39                                                                              C.sub.8 H.sub.17 'CFHCH.sub.2 O                                                           --  Ep1 --     Ph  2  L1 -- C.sub.10 H.sub.21                   40                                                                              C.sub.4 H.sub.9                                                                           --  Ep2 --     Ph  2  L1 -- C.sub.6 H.sub.13                    41                                                                              C.sub.6 H.sub.13                                                                          --  Gp1 --     Ph  2  L1 -- C.sub.12 H.sub.25                   42                                                                              C.sub.7 H.sub.15                                                                          --  Gp2 --     Ph  2  L1 -- C.sub.6 H.sub.13                    43                                                                              C.sub.6 H.sub.13                                                                          --  Cm1 --     Ph  2  L1 -- C.sub.8 H.sub.17                    44                                                                              C.sub.8 H.sub.17                                                                          --  Io1 --     Ph  2  L1 -- C.sub.6 H.sub.13                    45                                                                              C.sub.20 H.sub.41                                                                         --  Id1 --COO--                                                                              Ph  2  L1 -- C.sub.4 H.sub.9                     46                                                                              C.sub.11 H.sub.23                                                                         --  Id1 --     Ph  2  L1 -- C.sub.8 H.sub.17                    47                                                                              C.sub.8 H.sub.17                                                                          --  Id1 --     Ph  2  L1 -- C.sub.8 H.sub.17                    48                                                                              C.sub.5 H.sub.11                                                                          --  Id1 --     Ph2F                                                                              2  L1 -- C.sub.6 H.sub.13                    49                                                                              C.sub.6 H.sub.13                                                                          --  Tn  --     Ph  2  L1 -- C.sub.7 H.sub.15                    50                                                                              C.sub.4 H.sub.9 O                                                                         --  Tz2 --     Ph  2  L1 -- C.sub.9 H.sub.19                    51                                                                              C.sub.12 H.sub.25                                                                         --  Btb2                                                                              --     Ph  2  L1 -- C.sub.6 H.sub.13                    52                                                                              C.sub.6 H.sub.13 O                                                                        --  Btb2                                                                              --     Ph  2  L1 -- C.sub.9 H.sub.19                    53                                                                              CH.sub.2 ═CH(CH.sub.2).sub.3 O                                                        --  Ep2 --     Ph  2  L1 -- C.sub.6 H.sub.13                    54                                                                              C.sub.9 H.sub.19                                                                          --  Gp2 --     Ph  2  L1 -- C.sub.5 H.sub.11                    55                                                                              C.sub.5 H.sub.11 O                                                                        --  Np  --     Ph  2  L1 -- C.sub.10 H.sub.21                   56                                                                              C.sub.6 H.sub.13                                                                          Ph  Ph  --     Ph  2  L1 -- C.sub.3 H.sub.7                     57                                                                              F           Pr2 Ph  --     Ph  2  L1 -- C.sub.6 H.sub.13                    58                                                                              C.sub.3 H.sub.7                                                                           Py2 Ph  --     Ph  2  L1 -- C.sub.8 H.sub.17                    59                                                                              C.sub.5 H.sub.11                                                                          --  Ha2 --     Ph  2  L1 -- C.sub.11 H.sub.23                   60                                                                              C.sub.6 H.sub.13                                                                          Ph  Pr2 --     Ph  2  L1 -- C.sub.6 H.sub.13                    61                                                                              C.sub.9 H.sub.19                                                                          Ph  Pr1 --     Ph  2  L1 -- C.sub.5 H.sub.11                    62                                                                              C.sub.13 H.sub.27                                                                         Ph  Cy  --     Ph3Br                                                                             2  L1 -- C.sub.7 H.sub.15                    63                                                                              C.sub.10 H.sub.21 O                                                                       Ph  Py1 --     Ph  2  L1 -- C.sub.6 H.sub.13                    64                                                                              C.sub.7 H.sub.15                                                                          Ph  Py2 --     Ph  2  L1 -- C.sub.10 H.sub.21                   65                                                                              C.sub.4 H.sub.9                                                                           Ph3TF                                                                             Pa  --     Ph  2  L1 -- (CH.sub.2).sub.3 CH(CH.sub.3).s                                               ub.2                                66                                                                              H           --  Hb2 --     Ph  2  L1 -- C.sub.8 H.sub.17                    67                                                                              C.sub.8 H.sub.17                                                                          Ph  Tn  --     Ph  2  L1 -- C.sub.5 H.sub.11                    68                                                                              C.sub.2 H.sub.5                                                                           Ph  Tz1 --     Ph2M                                                                              2  L1 -- C.sub.3 H.sub.7                     69                                                                              C.sub.6 H.sub.13                                                                          Ph  Tz2 --     Ph  2  L1 -- C.sub.6 H.sub.13                    70                                                                              C.sub.10 H.sub.21                                                                         Ph  Td  --     Ph  2  L1 -- C.sub.7 H.sub.15                    71                                                                              C.sub.10 H.sub.21                                                                         --  Ph  --     Py1 2  L1 -- C.sub.6 H.sub.13                    72                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Py1 2  L1 -- C.sub.6 H.sub.13                    73                                                                              C.sub.6 H.sub.13 OCO                                                                      --  Ph  --     Py1 2  L1 -- C.sub.5 H.sub.11                    74                                                                              C.sub.7 H.sub.15                                                                          --  --  --     Pr2 2  L1 -- C.sub.10 H.sub.21                   75                                                                              C.sub.9 H.sub.19                                                                          --  Ph  --     Pr2 2  L1 -- C.sub.8 H.sub.17                    76                                                                              C.sub.3 H.sub.7                                                                           --  Ph  --     Pr2 2  L1 -- C.sub.6 H.sub.13                    77                                                                              C.sub.5 H.sub.11 O                                                                        --  --  --     Cy  2  L1 -- C.sub.4 H.sub.9                     78                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --CH.sub.2 O--                                                                       Cy  2  L1 -- C.sub.7 H.sub.15                    79                                                                              C.sub.12 H.sub.25                                                                         --  Ph  --     Cy  2  L1 -- C.sub.3 H.sub.7                     80                                                                              C.sub.6 H.sub.13 C.tbd.C                                                                  --  Ph  --     Pa  2  L1 -- C.sub.6 H.sub.13                    81                                                                              C.sub.8 H.sub.17 O                                                                        --  Ph  --     Pd  2  L1 -- C.sub.5 H.sub.11                    82                                                                              C.sub.3 H.sub.7                                                                           --  Ph2Cl                                                                             --     Tn  2  L1 -- C.sub.10 H.sub.21                   83                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --     Tn  2  L1 -- C.sub.7 H.sub.15                    84                                                                              C.sub.8 H.sub.17                                                                          --  Ph  --     Tz1 2  L1 -- C.sub.12 H.sub.25                   85                                                                              C.sub.4 H.sub.9 OCH(CH.sub.3)COO                                                          --  Ph  --     Tz1 2  L1 -- C.sub.5 H.sub.11                    86                                                                              C.sub.6 H.sub.13                                                                          --  Ph2F                                                                              --     Td  2  L1 -- (CH.sub.2).sub.3 CH(CH.sub.3)C.                                               sub.6 H.sub.13                      87                                                                              C.sub.5 H.sub.11                                                                          --  --  --     Np  2  L1 -- C.sub.9 H.sub.19                    88                                                                              C.sub.8 H.sub.17 OCH.sub.2 CH.sub.2                                                       --  Ph  --     Np  2  L1 -- C.sub.5 H.sub.11                    89                                                                              C.sub.11 H.sub.23                                                                         --  Ph  --     Np  2  L1 -- C.sub.6 H.sub.13                    90                                                                              C.sub.5 H.sub.11                                                                          --  --  --     Ep1 2  L1 -- C.sub.4 H.sub.9                     91                                                                              CH.sub.3    --  Ph  --     Ep1 2  L1 -- C.sub.7 H.sub.15                    92                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Ep1 2  L1 -- C.sub.6 H.sub.13                    93                                                                              C.sub.9 H.sub.19 O                                                                        --  --  --     Gp1 2  L1 -- C.sub.8 H.sub.17                    94                                                                              C.sub.8 H.sub.17                                                                          --  Ph  --     Gp1 2  L1 -- C.sub.10 H.sub.21                   95                                                                              C.sub.3 H.sub.7 COO                                                                       --  Ph  --     Gp1 2  L1 -- C.sub.11 H.sub.23                   96                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --     Id1 2  L1 -- C.sub.7 H.sub.15                    97                                                                              C.sub.12 H.sub.25                                                                         --  Ph  --     Io1 2  L1 -- C.sub.6 H.sub.13                    98                                                                              C.sub.10 H.sub.21                                                                         --  Ph  --     Cm1 2  L1 -- C.sub.5 H.sub.11                    99                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Ph  2  L1 -- (CH.sub.2).sub.4 C.sub.3                                                      F.sub.7                            100                                                                              C.sub.3 H.sub.7                                                                           Ph  Ph  --     Py1 2  L1 -- C.sub.7 H.sub.15                   101                                                                              C.sub.4 H.sub.9                                                                           Ph2CN                                                                             Ph  --     Pr1 2  L1 -- C.sub.4 H.sub.9                    102                                                                              C.sub.5 H.sub.11                                                                          Ph  Ph3F                                                                              --     Tz1 2  L1 -- C.sub.3 H.sub.7                    103                                                                              CN          Ph  Ph  --     Tn  2  L1 -- CH.sub.3                           104                                                                              C.sub.7 H.sub.15                                                                          Tn  Ph  --     Py1 2  L1 -- C.sub.8 H.sub.17                   105                                                                              C.sub.10 H.sub.21                                                                         Ph  Ph  --     Cy  2  L1 -- C.sub.6 H.sub.13                   106                                                                              C.sub.6 H.sub.13                                                                          --  --  --     Ph  8  L1 -- C.sub.8 H.sub.17                   107                                                                              C.sub.8 H.sub.17 O                                                                        --  --  --     Ph  12 L1 -- C.sub.18 H.sub.37                  108                                                                              C.sub.5 H.sub.11 O                                                                        --  --  --     Ph2F                                                                              4  L1 -- C.sub.6 H.sub.13                   109                                                                              CH.sub.3 O  --  Ph  --     Ph  3  L1 -- C.sub.6 H.sub.13                   110                                                                              C.sub.6 H.sub.13 'CHF(CH.sub.2).sub.2 O                                                   --  Ph  --     Ph  4  L1 -- C.sub.6 H.sub.13                   111                                                                              C.sub.7 H.sub.15 O                                                                        --  Ph  --     Ph23F                                                                             6  L1 -- C.sub.6 H.sub.13                   112                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --OCH.sub.2 --                                                                       Ph  11 L1 -- C.sub.9 H.sub.19                   113                                                                              C.sub.6 F.sub.13 CH.sub.2 O                                                               --  Pu  --C.tbd.C--                                                                          Ph  4  L1 -- C.sub.5 H.sub.11                   114                                                                              C.sub.8 H.sub.17 O                                                                        --  Ph  --COO--                                                                              Ph  6  L1 -- C.sub.6 H.sub.13                   115                                                                              C.sub.8 H.sub.17                                                                          --  Pr1 --     Ph  5  L1 -- C.sub.8 H.sub.17                   116                                                                              C.sub.10 H.sub.21                                                                         --  Pr2 --     Ph  4  L1 -- C.sub.4 H.sub.9                    117                                                                              C.sub.11 H.sub.23                                                                         --  Pr2 --     Ph  8  L1 -- C.sub.6 H.sub.13                   118                                                                              C.sub.12 H.sub.25                                                                         --  Pr2 --COO--                                                                              Ph  10 L1 -- C.sub.8 H.sub.17                   119                                                                              C.sub.4 H.sub.9 O                                                                         --  Py1 --     Ph  9  L1 -- C.sub.10 H.sub.21                  120                                                                              C.sub.13 H.sub.27                                                                         --  Py2 --     Ph  7  L1 -- C.sub.5 H.sub.11                   121                                                                              C.sub.6 H.sub.13 O                                                                        --  Py2 --     Ph  3  L1 -- C.sub.8 H.sub.17                   122                                                                              C.sub.6 H.sub.13 'CHFCH.sub.2 CH.sub.2                                                    --  Py2 --     Ph  4  L1 -- C.sub.9 H.sub.19                   123                                                                              C.sub.5 H.sub.11 O                                                                        --  Py2 --     Ph23F                                                                             4  L1 -- C.sub.4 H.sub.9                    124                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  6  L1 -- C.sub.6 H.sub.13                   125                                                                              C.sub.8 H.sub.17                                                                          --  Py2 --     Ph3F                                                                              7  L1 -- C.sub.7 H.sub.15                   126                                                                              C.sub.8 H.sub.17                                                                          --  Py2 --     Ph  4  L1 -- CH.sub.2 OC.sub.6 H.sub.13         127                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  8  L1 -- C.sub.6 H.sub.13                   128                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  5  L1 -- C.sub.6 H.sub.13                   129                                                                              C.sub.3 H.sub.7                                                                           --  Cy  --COO--                                                                              Ph  6  L1 -- C.sub.6 H.sub.13                   130                                                                              C.sub.5 H.sub.11                                                                          --  Pa  --     Ph  4  L1 -- C.sub.8 H.sub.17                   131                                                                              C.sub.10 H.sub.21                                                                         --  Pd  --     Ph  7  L1 -- C.sub.6 H.sub.13                   132                                                                              C.sub.6 H.sub.13                                                                          --  Dt2 --     Ph  9  L1 -- (CH.sub.2).sub.5 CH═CH.sub.                                               2                                  133                                                                              C.sub.8 H.sub.17                                                                          --  Tn  --     Ph  4  L1 -- C.sub.9 H.sub.19                   134                                                                              C.sub.5 H.sub.11                                                                          --  Tz1 --     Ph  8  L1 -- C.sub.8 H.sub.17                   135                                                                              C.sub.9 H.sub.19 O                                                                        --  Tz2 --     Ph  9  L1 -- C.sub.5 H.sub.11                   136                                                                              C.sub.2 H.sub.5                                                                           --  Td  --     Ph  8  L1 -- C.sub.8 H.sub.17                   137                                                                              C.sub.10 H.sub.21                                                                         --  Dx2 --     Ph  5  L1 -- C.sub.7 H.sub.15                   138                                                                              C.sub.6 H.sub.13                                                                          --  Boa2                                                                              --     Ph  4  L1 -- C.sub.10 H.sub.21                  139                                                                              C.sub.7 H.sub.15                                                                          --  Bob2                                                                              --     Ph  6  L1 -- C.sub.6 H.sub.13                   140                                                                              C.sub.16 H.sub.33 O                                                                       --  Bta2                                                                              --     Ph  4  L1 -- C.sub.6 H.sub.13                   141                                                                              C.sub.6 H.sub.13                                                                          --  Btb2                                                                              --     Ph  6  L1 -- C.sub.14 H.sub.29                  142                                                                              C.sub.5 H.sub.11                                                                          --  Np  --COO--                                                                              Ph  4  L1 -- C.sub.7 H.sub.15                   143                                                                              C.sub.8 H.sub.17 'CFHCH.sub.2 O                                                           --  Ep1 --     Ph  6  L1 -- C.sub.10 H.sub.21                  144                                                                              C.sub.4 H.sub.9                                                                           --  Ep2 --     Ph  8  L1 -- C.sub.6 H.sub.13                   145                                                                              C.sub.6 H.sub.13                                                                          --  Gp1 --     Ph  12 L1 -- C.sub.12 H.sub.25                  146                                                                              C.sub.7 H.sub.15                                                                          --  Gp2 --     Ph  7  L1 -- C.sub.6 H.sub.13                   147                                                                              C.sub.6 H.sub.13                                                                          --  Cm1 --     Ph  4  L1 -- C.sub.8 H.sub.17                   148                                                                              C.sub.8 H.sub.17                                                                          --  Io1 --     Ph  8  L1 -- C.sub.6 H.sub.13                   149                                                                              C.sub.20 H.sub.41                                                                         --  Id1 --COO--                                                                              Ph  4  L1 -- C.sub.4 H.sub.9                    150                                                                              C.sub.11 H.sub.23                                                                         --  Id1 --     Ph  9  L1 -- C.sub.8 H.sub.17                   151                                                                              C.sub.8 H.sub.17                                                                          --  Id1 --     Ph  10 L1 -- C.sub.8 H.sub.17                   152                                                                              C.sub.5 H.sub.11                                                                          --  Id1 --     Ph2F                                                                              3  L1 -- C.sub.6 H.sub.13                   153                                                                              C.sub.6 H.sub.13                                                                          --  Tn  --     Ph  4  L1 -- C.sub.7 H.sub.15                   154                                                                              C.sub.4 H.sub.9 O                                                                         --  Tz2 --     Ph  6  L1 -- C.sub.9 H.sub.19                   155                                                                              C.sub.12 H.sub.25                                                                         --  Btb2                                                                              --     Ph  8  L1 -- C.sub.6 H.sub.13                   156                                                                              C.sub.6 H.sub.13 O                                                                        --  Btb2                                                                              --     Ph  7  L1 -- C.sub.9 H.sub.19                   157                                                                              CH.sub.2 ═CH(CH.sub.2).sub.3 O                                                        --  Ep2 --     Ph  5  L1 -- C.sub.6 H.sub.13                   158                                                                              C.sub.9 H.sub.19                                                                          --  Gp2 --     Ph  4  L1 -- C.sub.5 H.sub.11                   159                                                                              C.sub.5 H.sub.11 O                                                                        --  Np  --     Ph  4  L1 -- C.sub.10 H.sub.21                  160                                                                              C.sub.6 H.sub.13                                                                          Ph  Ph  --     Ph  6  L1 -- C.sub.3 H.sub.7                    161                                                                              F           Pr2 Ph  --     Ph  8  L1 -- C.sub.6 H.sub.13                   162                                                                              C.sub.3 H.sub.7                                                                           Py2 Ph  --     Ph  9  L1 -- C.sub.8 H.sub.17                   163                                                                              C.sub.5 H.sub.11                                                                          --  Ha2 --     Ph  14 L1 -- C.sub.11 H.sub.23                  164                                                                              C.sub.6 H.sub.13                                                                          Ph  Pr2 --     Ph  3  L1 -- C.sub.6 H.sub.13                   165                                                                              C.sub.9 H.sub.19                                                                          Ph  Pr1 --     Ph  4  L1 -- C.sub.5 H.sub.11                   166                                                                              C.sub.13 H.sub.27                                                                         Ph  Cy  --     Ph3Br                                                                             6  L1 -- C.sub.7 H.sub.15                   167                                                                              C.sub.10 H.sub.21 O                                                                       Ph  Py1 --     Ph  4  L1 -- C.sub.6 H.sub.13                   168                                                                              C.sub.7 H.sub.15                                                                          Ph  Py2 --     Ph  6  L1 -- C.sub.10 H.sub.21                  169                                                                              C.sub.4 H.sub.9                                                                           Ph3TF                                                                             Pa  --     Ph  6  L1 -- (CH.sub.2).sub.3 CH(CH.sub.3).s                                               ub.2                               170                                                                              H           --  Hb2 --     Ph  8  L1 -- C.sub.8 H.sub.17                   171                                                                              C.sub.8 H.sub.17                                                                          Ph  Tn  --     Ph  10 L1 -- C.sub.5 H.sub.11                   172                                                                              C.sub.2 H.sub.5                                                                           Ph  Tz1 --     Ph2M                                                                              11 L1 -- C.sub.3 H.sub.7                    173                                                                              C.sub.6 H.sub.13                                                                          Ph  Tz2 --     Ph  4  L1 -- C.sub.6 H.sub.13                   174                                                                              C.sub.10 H.sub.21                                                                         Ph  Td  --     Ph  4  L1 -- C.sub.7 H.sub.15                   175                                                                              C.sub.10 H.sub.21                                                                         --  Ph  --     Py1 4  L1 -- C.sub.6 H.sub.13                   176                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Py1 5  L1 -- C.sub.5 H.sub.13                   177                                                                              C.sub.6 H.sub.13 OCO                                                                      --  Ph  --     Py1 6  L1 -- C.sub.5 H.sub.11                   178                                                                              C.sub.7 H.sub.15                                                                          --  --  --     Pr2 18 L1 -- C.sub.10 H.sub.21                  179                                                                              C.sub.9 H.sub.19                                                                          --  Ph  --     Pr2 4  L1 -- C.sub.8 H.sub.17                   180                                                                              C.sub.3 H.sub.7                                                                           --  Ph  --     Pr2 8  L1 -- C.sub.6 H.sub.13                   181                                                                              C.sub.5 H.sub.11 O                                                                        --  --  --     Cy  20 L1 -- C.sub.4 H.sub.9                    182                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --CH.sub.2 O--                                                                       Cy  4  L1 -- C.sub.7 H.sub.15                   183                                                                              C.sub.12 H.sub.25                                                                         --  Ph  --     Cy  6  L1 -- C.sub.3 H.sub.7                    184                                                                              C.sub.6 H.sub.13 C.tbd.C                                                                  --  Ph  --     Pa  5  L1 -- C.sub.6 H.sub.13                   185                                                                              C.sub.8 H.sub.17 O                                                                        --  Ph  --     Pd  7  L1 -- C.sub.5 H.sub.11                   186                                                                              C.sub.3 H.sub.7                                                                           --  Ph2Cl                                                                             --     Tn  13 L1 -- C.sub.10 H.sub.21                  187                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --     Tn  4  L1 -- C.sub.7 H.sub.15                   188                                                                              C.sub.8 H.sub.17                                                                          --  Ph  --     Tz1 6  L1 -- C.sub.12 H.sub.25                  189                                                                              C.sub.4 H.sub.9 OCH(CH.sub.3)COO                                                          --  Ph  --     Tz1 4  L1 -- C.sub.5 H.sub.11                   190                                                                              C.sub.6 H.sub.13                                                                          --  Ph2F                                                                              --     Td  4  L1 -- (CH.sub.2).sub.3 CH(CH.sub.3)C.                                               sub.6 H.sub.13                     191                                                                              C.sub.5 H.sub.11                                                                          --  --  --     Np  6  L1 -- C.sub.9 H.sub.19                   192                                                                              C.sub.8 H.sub.17 OCH.sub.2 CH.sub.2                                                       --  Ph  --     Np  6  L1 -- C.sub.5 H.sub.11                   193                                                                              C.sub.11 H.sub.23                                                                         --  Ph  --     Np  8  L1 -- C.sub.6 H.sub.13                   194                                                                              C.sub.5 H.sub.11                                                                          --  --  --     Ep1 8  L1 -- C.sub.4 H.sub.9                    195                                                                              CH.sub.3    --  Ph  --     Ep1 9  L1 -- C.sub.7 H.sub.15                   196                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Ep1 10 L1 -- C.sub.6 H.sub.13                   197                                                                              C.sub.9 H.sub.19 O                                                                        --  --  --     Gp1 4  L1 -- C.sub.8 H.sub.17                   198                                                                              C.sub.8 H.sub.17                                                                          --  Ph  --     Gp1 5  L1 -- C.sub.10 H.sub.21                  199                                                                              C.sub.3 H.sub.7 COO                                                                       --  Ph  --     Gp1 7  L1 -- C.sub.11 H.sub.23                  200                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --     Id1 12 L1 -- C.sub.7 H.sub.15                   201                                                                              C.sub.12 H.sub.25                                                                         --  Ph  --     Io1 4  L1 -- C.sub.6 H.sub.13                   202                                                                              C.sub.10 H.sub.21                                                                         --  Ph  --     Cm1 4  L1 -- C.sub.5 H.sub.11                   203                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Ph  6  L1 -- (CH.sub.2).sub.4 C.sub.3                                                      F.sub.7                            204                                                                              C.sub.3 H.sub.7                                                                           Ph  Ph  --     Py1 8  L1 -- C.sub.7 H.sub.15                   205                                                                              C.sub.4 H.sub.9                                                                           Ph2CN                                                                             Ph  --     Pr1 7  L1 -- C.sub.4 H.sub.9                    206                                                                              C.sub.5 H.sub.11                                                                          Ph  Ph3F                                                                              --     Tz1 4  L1 -- C.sub.3 H.sub.7                    207                                                                              CN          Ph  Ph  --     Tn  6  L1 -- CH.sub.3                           208                                                                              C.sub.7 H.sub.15                                                                          Tn  Ph  --     Py1 4  L1 -- C.sub.8 H.sub.17                   209                                                                              C.sub.10 H.sub.21                                                                         Ph  Ph  --     Cy  4  L1 -- C.sub.5 H.sub.13                   211                                                                              C.sub.6 H.sub.13                                                                          --  --  --     Ph  2  L1 Ph H                                  212                                                                              C.sub.8 H.sub.17 O                                                                        --  --  --     Ph  8  L2 Ph OCH.sub.3                          213                                                                              C.sub.5 H.sub.11 O                                                                        --  --  --     Ph2F                                                                              2  L1 Ph2F                                                                             C.sub.6 H.sub.13                   214                                                                              CH.sub.3 O  --  Ph  --     Ph  4  L2 Ph H                                  215                                                                              C.sub.6 H.sub.13 'CHF(CH.sub.2).sub.2 O                                                   --  Ph  --     Ph  2  L1 Ph C.sub.6 H.sub.13                   216                                                                              C.sub.7 H.sub.15 O                                                                        --  Ph  --     Ph23F                                                                             2  L1 Ph C.sub.6 H.sub.13                   217                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --OCH.sub.2 --                                                                       Ph  4  L1 Ph H                                  218                                                                              C.sub.6 F.sub.13 CH.sub.2 O                                                               --  Ph  --C.tbd.C--                                                                          Ph  2  L1 Ph C.sub.5 H.sub.11                   219                                                                              C.sub.8 H.sub.17 O                                                                        --  Ph  --COO--                                                                              Ph  7  L2 Pr1                                                                              H                                  220                                                                              C.sub.8 H.sub.17                                                                          --  Pr1 --     Ph  7  L2 Ph OCH.sub.3                          221                                                                              C.sub.10 H.sub.21                                                                         --  Pr2 --     Ph  2  L1 Ph H                                  222                                                                              C.sub.11 H.sub.23                                                                         --  Pr2 --     Ph  4  L1 Ph C.sub.6 H.sub.13                   223                                                                              C.sub.12 H.sub.25                                                                         --  Pr2 --COO--                                                                              Ph  8  L2 Ph OC.sub.6 H.sub.13                  224                                                                              C.sub.4 H.sub.9 O                                                                         --  Py1 --     Ph  2  L1 Cy H                                  225                                                                              C.sub.13 H.sub.27                                                                         --  Py2 --     Ph  2  L1 Ph C.sub.5 H.sub.11                   226                                                                              C.sub.6 H.sub.13 O                                                                        --  Py2 --     Ph  6  L2 Ph C.sub.6 H.sub.13                   227                                                                              C.sub.6 H.sub.13 'CHFCH.sub.2 O                                                           --  Py2 --     Ph  4  L2 Ph H                                  228                                                                              C.sub.5 H.sub.11 O                                                                        --  Py2 --     Ph23F                                                                             2  L1 Ph C.sub.4 H.sub.9                    229                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  2  L1 Ph H                                  230                                                                              C.sub.8 H.sub.17                                                                          --  Py2 --     Ph3F                                                                              2  L1 Ph C.sub.6 H.sub.13                   231                                                                              C.sub.6 H.sub.13                                                                          --  Cy  --     Ph  4  L2 Ph C.sub.2 H.sub.4 OC.sub.4                                                      H.sub.9                            232                                                                              C.sub.8 H.sub.17 OCO                                                                      --  Cy  --     Ph  2  L1 Pd H                                  233                                                                              C.sub.6 H.sub.13                                                                          --  Cy  --CH═CH--                                                                        Ph  5  L1 Ph OC.sub.10 H.sub.21                 234                                                                              C.sub.3 H.sub.7                                                                           --  Cy  --COO--                                                                              Ph  2  L1 Tz2                                                                              H                                  235                                                                              C.sub.5 H.sub.11                                                                          --  Pa  --     Ph  5  L2 Ph C.sub.8 H.sub.17                   236                                                                              C.sub.10 H.sub.21                                                                         --  Pd  --     Ph  2  L1 Ph OCH.sub.3                          237                                                                              C.sub.6 H.sub.13                                                                          --  Dt2 --     Ph  6  L2 Ph (CH.sub.2).sub.5 CH═CH.sub.                                               2                                  238                                                                              C.sub.8 H.sub.17                                                                          --  Tn  --     Ph  2  L1 Ph H                                  239                                                                              C.sub.5 H.sub.11                                                                          --  Tz1 --     Ph  2  L1 Ph H                                  240                                                                              C.sub.6 H.sub.13 'CHFCH.sub.2 CH.sub.2                                                    --  Py2 --     Ph  4  L1 Py1                                                                              H                                  241                                                                              C.sub.9 H.sub.19 O                                                                        --  Tz2 --     Ph  2  L1 Ph C.sub.6 H.sub.13                   242                                                                              C.sub.2 H.sub.5                                                                           --  Td  --     Ph  2  L2 Ph H                                  243                                                                              C.sub.10 H.sub.21                                                                         --  Dx2 --     Ph  4  L2 Ph C.sub.7 H.sub.15                   244                                                                              C.sub.6 H.sub.13                                                                          --  Boa2                                                                              --     Ph  2  L1 Ph H                                  245                                                                              C.sub.7 H.sub.15                                                                          --  Bob2                                                                              --     Ph  2  L1 Ph OCH.sub.3                          246                                                                              C.sub.16 H.sub.33 O                                                                       --  Bta2                                                                              --     Ph  2  L1 Ph H                                  247                                                                              C.sub.6 H.sub.13                                                                          --  Btb2                                                                              --     Ph  4  L2 Tn C.sub.14 H.sub.29                  248                                                                              C.sub.5 H.sub.11                                                                          --  Np  --COO--                                                                              Ph  2  L1 Ph H                                  249                                                                              C.sub.8 H.sub.17 'C(CF.sub.3)HCH.sub.2 O                                                  --  Ep1 --     Ph  2  L1 Ph H                                  250                                                                              C.sub.4 H.sub.9                                                                           --  Ep2 --     Ph  2  L1 Ph C.sub.6 H.sub.13                   251                                                                              C.sub.6 H.sub.13                                                                          --  Gp1 --     Ph  6  L2 Ph OCH.sub.3                          252                                                                              C.sub.7 H.sub.15                                                                          --  Gp2 --     Ph  2  L1 Ph H                                  253                                                                              C.sub.6 H.sub.13                                                                          --  Cm1 --     Ph  10 L2 Ph C.sub.6 H.sub.13                   254                                                                              C.sub.8 H.sub.17                                                                          --  Io1 --     Ph  4  L1 Ph H                                  255                                                                              C.sub.20 H.sub.41                                                                         --  Id1 --COO--                                                                              Ph  2  L1 Ph C.sub.4 H.sub.9                    256                                                                              C.sub.11 H.sub.23                                                                         --  Id1 --     Ph  4  L2 Ph H                                  257                                                                              C.sub.8 H.sub.17                                                                          --  Id1 --     Ph  2  L1 Ph H                                  258                                                                              C.sub.5 H.sub.11                                                                          --  Id1 --     Ph2F                                                                              2  L1 Ph C.sub.6 H.sub.13                   259                                                                              C.sub.6 H.sub.13                                                                          --  Tn  --     Ph  8  L2 Ph C.sub.7 H.sub.15                   260                                                                              C.sub.4 H.sub.9 O                                                                         --  Tz2 --     Ph  2  L1 Ph C.sub.9 H.sub.19                   261                                                                              C.sub.12 H.sub.25                                                                         --  Btb2                                                                              --     Ph  9  L1 Ph H                                  262                                                                              C.sub.6 H.sub.13 O                                                                        --  Btb2                                                                              --     Ph  2  L1 Ph C.sub.6 H.sub.13                   263                                                                              CH.sub.2 ═CH(CH.sub.2).sub.5 O                                                        --  Ep2 --     Ph  7  L2 Ph H                                  264                                                                              C.sub.9 H.sub.19                                                                          --  Gp2 --     Ph  2  L1 Ph OCH.sub.3                          265                                                                              C.sub.5 H.sub.11 O                                                                        --  Np  --     Ph  2  L1 Np C.sub.10 H.sub.21                  266                                                                              C.sub.6 H.sub.13                                                                          Ph  Ph  --     Ph  2  L1 Ph C.sub.3 H.sub.7                    267                                                                              F           Pr2 Ph  --     Ph  2  L1 Ph H                                  268                                                                              C.sub.3 H.sub.7                                                                           Py2 Ph  --     Ph  7  L1 Ph H                                  269                                                                              C.sub.5 H.sub.11                                                                          --  Ha2 --     Ph  7  L2 Ph C.sub.11 H.sub.23                  270                                                                              C.sub.6 H.sub.13                                                                          Ph  Pr2 --     Ph  4  L2 Ph H                                  271                                                                              C.sub.9 H.sub.19                                                                          Ph  Pr1 --     Ph  2  L1 Ph C.sub.6 H.sub.13                   272                                                                              C.sub.13 H.sub.27                                                                         Ph  Cy  --     Ph3Br                                                                             2  L1 Ph C.sub.7 H.sub.15                   273                                                                              C.sub.10 H.sub.21 O                                                                       Ph  Py1 --     Ph  2  L1 Ph H                                  274                                                                              C.sub.7 H.sub.15                                                                          Ph  Py2 --     Ph  2  L1 Ph C.sub.10 H.sub.21                  275                                                                              C.sub.4 H.sub.9                                                                           Ph3TF                                                                             Pa  --     Ph  6  L2 Ph C.sub.6 H.sub.13                   276                                                                              H           --  Hb2 --     Ph  2  L1 Ph H                                  277                                                                              C.sub.8 H.sub.17                                                                          Ph  Tn  --     Ph  4  L1 Ph3F                                                                             C.sub.5 H.sub.11                   278                                                                              C.sub.2 H.sub.5                                                                           Ph  Tz1 --     Ph2M                                                                              2  L1 Ph H                                  279                                                                              C.sub.6 H.sub.13                                                                          Ph  Tz2 --     Ph  8  L2 Ph H                                  280                                                                              C.sub.10 H.sub.21                                                                         Ph  Td  --     Ph  2  LM1                                                                              Ph C.sub.6 H.sub.13                   281                                                                              C.sub.10 H.sub.21                                                                         --  Ph  --     Py1 2  L1 Ph H                                  282                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Py1 3  L2 Ph C.sub.6 H.sub.13                   283                                                                              C.sub.6 H.sub.13 OCO                                                                      --  Ph  --     Py1 2  L1 Ph H                                  284                                                                              C.sub.7 H.sub.15                                                                          --  --  --     Pr2 2  L1 Ph C.sub.6 H.sub.13                   285                                                                              C.sub.9 H.sub.19                                                                          --  Ph  --     Pr2 6  L2 Ph H                                  286                                                                              C.sub.3 H.sub.7                                                                           --  Ph  --     Pr2 2  L1 Ph OCH.sub.3                          287                                                                              C.sub.5 H.sub.11 O                                                                        --  --  --     Cy  6  L1 Ep1                                                                              H                                  288                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --CH.sub.2 O--                                                                       Cy  2  L1 Ph C.sub.7 H.sub.15                   289                                                                              C.sub.12 H.sub.25                                                                         --  Ph  --     Cy  4  L2 Ph H                                  290                                                                              C.sub.6 H.sub.13 C.tbd.C                                                                  --  Ph  --     Pa  2  L1 Ph H                                  291                                                                              C.sub.8 H.sub.17 O                                                                        --  Ph  --     Pd  8  L2 Ph C.sub.5 H.sub.11                   292                                                                              C.sub.3 H.sub.7                                                                           --  Ph2Cl                                                                             --     Tn  2  L1 Ph H                                  293                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --     Tn  2  L1 Ph H                                  294                                                                              C.sub.8 H.sub.17                                                                          --  Ph  --     Tz1 2  L1 Ph H                                  295                                                                              C.sub.4 H.sub.9 OCH(CH.sub.3)COO                                                          --  Ph  --     Tz1 6  L1 Ph C.sub.5 H.sub.11                   296                                                                              C.sub.6 H.sub.13                                                                          --  Ph2F                                                                              --     Td  2  L1 Ph C.sub.6 H.sub.13                   297                                                                              C.sub.5 H.sub.11                                                                          --  --  --     Np  2  L1 Gp1                                                                              H                                  298                                                                              C.sub.8 H.sub.17 OCH.sub.2 CH.sub.2                                                       --  Ph  --     Np  5  L2 Ph C.sub.5 H.sub.11                   299                                                                              C.sub.11 H.sub.23                                                                         --  Ph  --     Np  2  L1 Ph C.sub.6 H.sub.13                   300                                                                              C.sub.5 H.sub.11                                                                          --  --  --     Ep1 2  L1 Ph OC.sub.4 H.sub.9                   301                                                                              CH.sub.3    --  Ph  --     Ep1 7  L2 Ph C.sub.7 H.sub.15                   302                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Ep1 2  L1 Ph H                                  303                                                                              C.sub.9 H.sub.19 O                                                                        --  --  --     Gp1 2  L1 Ph C.sub.6 H.sub.13                   304                                                                              C.sub.8 H.sub.17                                                                          --  Ph  --     Gp1 4  L1 Ph H                                  305                                                                              C.sub.3 H.sub.7 COO                                                                       --  Ph  --     Gp1 8  L2 Ph OCH.sub.3                          306                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --     Id1 2  L1 Ph H                                  307                                                                              C.sub.12 H.sub.25                                                                         --  Ph  --     Io1 2  L1 Ph C.sub.6 H.sub.13                   308                                                                              C.sub.10 H.sub.21                                                                         --  Ph  --     Cm1 2  L2 Ph H                                  309                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Ph  2  L1 Ph C.sub.6 H.sub.13                   310                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  2  LM1                                                                              -- C.sub.7 H.sub.15                   311                                                                              C.sub.8 H.sub.17                                                                          --  Py2 --     Ph  4  LM1                                                                              -- C.sub.6 H.sub.13                   312                                                                              C.sub.5 H.sub.11                                                                          --  Ph  --     Ph  2  LM1                                                                              -- C.sub.5 H.sub.11                   313                                                                              C.sub.6 H.sub.13                                                                          Py2 Ph  --     Ph  3  LM1                                                                              -- C.sub.8 H.sub.17                   314                                                                              C.sub.7 H.sub.15                                                                          --  Ph  --     Ph  6  LM2                                                                              -- C.sub.8 H.sub.17                   315                                                                              C.sub.10 H.sub.21                                                                         Py2 Ph  --     Ph  2  LM2                                                                              -- C.sub.6 H.sub.13                   316                                                                              C.sub.6 H.sub.13                                                                          --  --  --     Ph  10 L2 -- C.sub.8 H.sub.17                   317                                                                              C.sub.8 H.sub.17 O                                                                        --  --  --     Ph  8  L2 -- C.sub.18 H.sub.37                  318                                                                              C.sub.5 H.sub.11 O                                                                        --  --  --     Ph2F                                                                              6  L2 -- C.sub.6 H.sub.13                   319                                                                              CH.sub.3 O  --  Ph  --     Ph  4  L2 -- C.sub.6 H.sub.13                   320                                                                              C.sub.5 H.sub.11 'CHF(CH.sub.2).sub.2 O                                                   --  Ph  --     Ph  8  L2 -- C.sub.6 H.sub.13                   321                                                                              C.sub.7 H.sub.15 O                                                                        --  Ph  --     Ph23F                                                                             12 L2 -- C.sub.6 H.sub.13                   322                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --OCH.sub.2 --                                                                       Ph  4  L2 -- C.sub.9 H.sub.19                   323                                                                              C.sub.6 F.sub.13 CH.sub.2 O                                                               --  Ph  --C.tbd.C--                                                                          Ph  6  L2 -- C.sub.5 H.sub.11                   324                                                                              C.sub.8 H.sub.17 O                                                                        --  Ph  --COO--                                                                              Ph  8  L2 -- C.sub.6 H.sub.13                   325                                                                              C.sub.8 H.sub.17                                                                          --  Pr1 --     Ph  9  L2 -- C.sub.8 H.sub.17                   326                                                                              C.sub.10 H.sub.21                                                                         --  Pr2 --     Ph  6  L2 -- C.sub.4 H.sub.9                    327                                                                              C.sub.11 H.sub.23                                                                         --  Pr2 --     Ph  4  L2 -- C.sub.6 H.sub.13                   328                                                                              C.sub.12 H.sub.25                                                                         --  Pr2 --COO--                                                                              Ph  5  L2 -- C.sub.8 H.sub.17                   329                                                                              C.sub.4 H.sub.9 O                                                                         --  Py1 --     Ph  6  L2 -- C.sub.10 H.sub.21                  330                                                                              C.sub.13 H.sub.27                                                                         --  Py2 --     Ph  2  L2 -- C.sub.5 H.sub.11                   331                                                                              C.sub.6 H.sub.13 O                                                                        --  Py2 --     Ph  4  L2 -- C.sub.8 H.sub.17                   332                                                                              C.sub.6 H.sub.13 '(CF.sub.3)CH.sub.2 O                                                    --  Py2 --     Ph  6  L2 -- C.sub.9 H.sub.19                   333                                                                              C.sub.5 H.sub.11 O                                                                        --  Py2 --     Ph23F                                                                             8  L2 -- C.sub.4 H.sub.9                    334                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  2  L2 -- C.sub.6 H.sub.13                   335                                                                              C.sub.8 H.sub.17                                                                          --  Py2 --     Ph3F                                                                              7  L2 -- C.sub.7 H.sub.15                   336                                                                              C.sub.6 H.sub.13                                                                          --  Cy  --     Ph  8  L2 -- C.sub.3 H.sub.6 OC.sub.4                                                      H.sub.9                            337                                                                              C.sub.6 H.sub.13 OCO                                                                      --  Cy  --     Ph  2  L2 -- C.sub.14 H.sub.29                  338                                                                              C.sub.6 H.sub.13                                                                          --  Cy  --CH═CH--                                                                        Ph  5  L2 -- C.sub.10 H.sub.21                  339                                                                              C.sub.3 H.sub.7                                                                           --  Cy  --COO--                                                                              Ph  6  L2 -- C.sub.6 H.sub.13                   340                                                                              C.sub.5 H.sub.11                                                                          --  Pa  --     Ph  4  L2 -- C.sub.8 H.sub.17                   341                                                                              C.sub.10 H.sub.21                                                                         --  Pd  --     Ph  5  L2 -- C.sub.6 H.sub.13                   342                                                                              C.sub.6 H.sub.13                                                                          --  Dt2 --     Ph  3  L2 -- (CH.sub.2).sub.2 CH═CH.sub.                                               2                                  343                                                                              C.sub.8 H.sub.17                                                                          --  Tn  --     Ph  8  L2 -- C.sub.9 H.sub.19                   344                                                                              C.sub.6 H.sub.13 'CHFCH.sub.2 CH.sub.2                                                    --  Py2 --     Ph  4  L2 -- C.sub.6 H.sub.13                   345                                                                              C.sub.5 H.sub.11                                                                          --  Tz1 --     Ph  6  L2 -- C.sub.8 H.sub.17                   346                                                                              C.sub.9 H.sub.19 O                                                                        --  Tz2 --     Ph  4  L2 -- C.sub.5 H.sub.11                   347                                                                              C.sub.2 H.sub.5                                                                           --  Td  --     Ph  8  L2 -- C.sub.8 H.sub.17                   348                                                                              C.sub.10 H.sub.21                                                                         --  Dx2 --     Ph  10 L2 -- C.sub.7 H.sub.15                   349                                                                              C.sub.6 H.sub.13                                                                          --  Boa2                                                                              --     Ph  11 L2 -- C.sub.10 H.sub.21                  350                                                                              C.sub.7 H.sub.15                                                                          --  Bob2                                                                              --     Ph  2  L2 -- C.sub.6 H.sub.13                   351                                                                              C.sub.16 H.sub.33 O                                                                       --  Bta2                                                                              --     Ph  4  L2 -- C.sub.6 H.sub.13                   352                                                                              C.sub.6 H.sub.13                                                                          --  Btb2                                                                              --     Ph  6  L2 -- C.sub.14 H.sub.29                  353                                                                              C.sub.5 H.sub.11                                                                          --  Np  --COO--                                                                              Ph  8  L2 -- C.sub.7 H.sub.15                   354                                                                              C.sub.8 H.sub.17 'CFHCH.sub.2 O                                                           --  Ep1 --     Ph  5  L2 -- C.sub.10 H.sub.21                  355                                                                              C.sub.4 H.sub.9                                                                           --  Ep2 --     Ph  2  L2 -- C.sub.6 H.sub.13                   356                                                                              C.sub.6 H.sub.13                                                                          --  Gp1 --     Ph  3  L2 -- C.sub.12 H.sub.25                  357                                                                              C.sub.7 H.sub.15                                                                          --  Gp2 --     Ph  6  L2 -- C.sub.6 H.sub.13                   358                                                                              C.sub.6 H.sub.13                                                                          --  Cm1 --     Ph  4  L2 -- C.sub.8 H.sub.17                   359                                                                              C.sub.8 H.sub.17                                                                          --  Io1 --     Ph  8  L2 -- C.sub.6 H.sub.13                   360                                                                              C.sub.20 H.sub.41                                                                         --  Id1 --COO--                                                                              Ph  10 L2 -- C.sub.4 H.sub.9                    361                                                                              C.sub.11 H.sub.23                                                                         --  Id1 --     Ph  2  L2 -- C.sub.8 H.sub.17                   362                                                                              C.sub.8 H.sub.17                                                                          --  Id1 --     Ph  4  L2 -- C.sub.8 H.sub.17                   363                                                                              C.sub.5 H.sub.11                                                                          --  Id1 --     Ph2F                                                                              6  L2 -- C.sub.6 H.sub.13                   364                                                                              C.sub.6 H.sub.13                                                                          --  Tn  --     Ph  18 L2 -- C.sub.7 H.sub.15                   365                                                                              C.sub.4 H.sub.9 O                                                                         --  Tz2 --     Ph  9  L2 -- C.sub.9 H.sub.19                   366                                                                              C.sub.12 H.sub.25                                                                         --  Btb2                                                                              --     Ph  8  L2 -- C.sub.6 H.sub.13                   367                                                                              C.sub.6 H.sub.13 O                                                                        --  Btb2                                                                              --     Ph  5  L2 -- C.sub.9 H.sub.19                   368                                                                              CH.sub.2 ═CH(CH.sub.2).sub.8 O                                                        --  Ep2 --     Ph  4  L2 -- C.sub.6 H.sub.13                   369                                                                              C.sub.9 H.sub.19                                                                          --  Gp2 --     Ph  4  L2 -- C.sub.5 H.sub.11                   370                                                                              C.sub.5 H.sub.11 O                                                                        --  Np  --     Ph  6  L2 -- C.sub.10 H.sub.21                  371                                                                              C.sub.6 H.sub.13                                                                          Ph  Ph  --     Ph  2  L2 -- C.sub.3 H.sub.7                    372                                                                              F           Pr2 Ph  --     Ph  5  L2 -- C.sub.6 H.sub.13                   373                                                                              C.sub.3 H.sub.7                                                                           Py2 Ph  --     Ph  2  L2 -- C.sub.8 H.sub.17                   374                                                                              C.sub.5 H.sub.11                                                                          --  Ha2 --     Ph  5  L2 -- C.sub.11 H.sub.23                  375                                                                              C.sub.6 H.sub.13                                                                          Ph  Pr2 --     Ph  6  L2 -- C.sub.6 H.sub.13                   376                                                                              C.sub.9 H.sub.19                                                                          Ph  Pr1 --     Ph  8  L2 -- C.sub.5 H.sub.11                   377                                                                              C.sub.13 H.sub.27                                                                         Ph  Cy  --     Ph3Br                                                                             9  L2 -- C.sub.7 H.sub.15                   378                                                                              C.sub.10 H.sub.21 O                                                                       Ph  Py1 --     Ph  4  L2 -- C.sub.6 H.sub.13                   379                                                                              C.sub.7 H.sub.15                                                                          Ph  Py2 --     Ph  6  L2 -- C.sub.10 H.sub.21                  380                                                                              C.sub.4 H.sub.9                                                                           Ph3TF                                                                             Pa  --     Ph  7  L2 -- (CH.sub.2).sub.5 CH(CH.sub.3).s                                               ub.2                               381                                                                              H           --  Hb2 --     Ph  8  L2 -- C.sub.8 H.sub.17                   382                                                                              C.sub.8 H.sub.17                                                                          Ph  Tn  --     Ph  8  L2 -- C.sub.5 H.sub.11                   383                                                                              C.sub.2 H.sub.5                                                                           Ph  Tz1 --     Ph2M                                                                              3  L2 -- C.sub.3 H.sub.7                    384                                                                              C.sub.6 H.sub.13                                                                          Ph  Tz2 --     Ph  4  L2 -- C.sub.6 H.sub.13                   385                                                                              C.sub.10 H.sub.21                                                                         Ph  Td  --     Ph  6  L2 -- C.sub.7 H.sub.15                   386                                                                              C.sub.10 H.sub.21                                                                         --  Ph  --     Py1 2  L2 -- C.sub.6 H.sub.13                   387                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Py1 4  L2 -- C.sub.6 H.sub.13                   388                                                                              C.sub.6 H.sub.13 OCO                                                                      --  Ph  --     Py1 6  L2 -- C.sub.5 H.sub.11                   389                                                                              C.sub.7 H.sub.15                                                                          --  --  --     Pr2 4  L2 -- C.sub.10 H.sub.21                  390                                                                              C.sub.9 H.sub.19                                                                          --  Ph  --     Pr2 8  L2 -- C.sub.8 H.sub.17                   391                                                                              C.sub.3 H.sub.7                                                                           --  Ph  --     Pr2 11 L2 -- C.sub.5 H.sub.13                   392                                                                              C.sub.5 H.sub.11 O                                                                        --  --  --     Cy  4  L2 -- C.sub.4 H.sub.9                    393                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --CH.sub.2 O--                                                                       Cy  6  L2 -- C.sub.7 H.sub.15                   394                                                                              C.sub.12 H.sub.25                                                                         --  Ph  --     Cy  8  L2 -- C.sub.3 H.sub.7                    395                                                                              C.sub.6 H.sub.13 C.tbd.C                                                                  --  Ph  --     Pa  9  L2 -- C.sub.6 H.sub.13                   396                                                                              C.sub.8 H.sub.17 O                                                                        --  Ph  --     Pd  4  L2 -- C.sub.5 H.sub.11                   397                                                                              C.sub.3 H.sub.7                                                                           --  Ph2Cl                                                                             --     Tn  5  L2 -- C.sub.10 H.sub.21                  398                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --     Tn  6  L2 -- C.sub.7 H.sub.15                   399                                                                              C.sub.8 H.sub.17                                                                          --  Ph  --     Tz1 8  L2 -- C.sub.12 H.sub.25                  400                                                                              C.sub.4 H.sub.9 OCH(CH.sub.3)COO                                                          --  Ph  --     Tz1 4  L2 -- C.sub.5 H.sub.11                   401                                                                              C.sub.6 H.sub.13                                                                          --  Ph2F                                                                              --     Td  6  L2 -- CH.sub.2 CH(CH.sub.3)C.sub.6                                                  H.sub.13                           402                                                                              C.sub.5 H.sub.11                                                                          --  --  --     Np  8  L2 -- C.sub.9 H.sub.19                   402                                                                              C.sub.8 H.sub.17 OCH.sub.2 CH.sub.2                                                       --  Ph  --     Np  7  L2 -- C.sub.5 H.sub.11                   404                                                                              C.sub.11 H.sub.23                                                                         --  Ph  --     Np  10 L2 -- C.sub.5 H.sub.13                   405                                                                              C.sub.5 H.sub.11                                                                          --  --  --     Ep1 15 L2 -- C.sub.4 H.sub.9                    406                                                                              CH.sub.3    --  Ph  --     Ep1 2  L2 -- C.sub.7 H.sub.15                   407                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Ep1 4  L2 -- C.sub.6 H.sub.13                   408                                                                              C.sub.9 H.sub.19 O                                                                        --  --  --     Gp1 14 L2 -- C.sub.8 H.sub.17                   409                                                                              C.sub.8 H.sub.17                                                                          --  Ph  --     Gp1 3  L2 -- C.sub.10 H.sub.21                  410                                                                              C.sub.3 H.sub.7 COO                                                                       --  Ph  --     Gp1 4  L2 -- C.sub.11 H.sub.23                  411                                                                              C.sub.4 H.sub.9                                                                           --  Ph  --     Id1 6  L2 -- C.sub.7 H.sub.15                   412                                                                              C.sub.12 H.sub.25                                                                         --  Ph  --     Io1 8  L2 -- C.sub.6 H.sub.13                   413                                                                              C.sub.10 H.sub.21                                                                         --  Ph  --     Cm1 4  L2 -- C.sub.5 H.sub.11                   414                                                                              C.sub.6 H.sub.13                                                                          --  Ph  --     Ph  6  L2 -- (CH.sub.2).sub.2 C.sub.4                                                      F.sub.9                            415                                                                              C.sub.3 H.sub.7                                                                           Ph  Ph  --     Py1 8  L2 -- C.sub.7 H.sub.15                   416                                                                              C.sub.4 H.sub.9                                                                           Ph2CN                                                                             Ph  --     Pr1 3  L2 -- C.sub.4 H.sub.9                    417                                                                              C.sub.5 H.sub.11                                                                          Ph  Ph3F                                                                              --     Tz1 8  L2 -- C.sub.3 H.sub.7                    418                                                                              CN          Ph  Ph  --     Tn  4  L2 -- CH.sub.3                           419                                                                              C.sub.7 H.sub.15                                                                          Tn  Ph  --     Py1 6  L2 -- C.sub.8 H.sub.17                   420                                                                              C.sub.10 H.sub.11                                                                         Ph  Ph  --     Cy  8  L2 -- C.sub.6 H.sub.13                   421                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  --  --     Ph  2  L1 -- C.sub.8 H.sub.17                   422                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  --  --     Ph  4  L2 -- C.sub.18 H.sub.37                  423                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      --  --  --     PH2F                                                                              6  L1 Ph C.sub.6 H.sub.13                   424                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      --  Ph  --     Ph  2  L1 -- C.sub.6 H.sub.13                   425                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Ph  --     Ph  2  L1 -- C.sub.6 H.sub.13                   426                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Ph  --     Ph23F                                                                             4  L2 -- C.sub.6 H.sub.13                   427                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Ph  --OCH.sub.2 --                                                                       Ph  2  L1 -- C.sub.9 H.sub.19                   428                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      --  Ph  --C.tbd.C--                                                                          Ph  2  L1 Ph H                                  429                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Ph  --COO--                                                                              Ph  3  L1 -- C.sub.5 H.sub.13                   430                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Pr1 --     Ph  2  L1 -- C.sub.8 H.sub.17                   431                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Pr2 --     Ph  4  L1 Ph OCH.sub.2 C.sub.6 F.sub.13         432                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      --  Pr2 --     Ph  5  L2 -- C.sub.6 H.sub.13                   433                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Pr2 --COO--                                                                              Ph  2  L1 -- C.sub.8 H.sub.17                   434                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Py1 --     Ph  2  L1 -- C.sub.10 H.sub.21                  435                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      --  Py2 --     Ph  6  L2 -- C.sub.5 H.sub.11                   436                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Ph  --     Py1 8  L1 -- C.sub.8 H.sub.17                   437                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Py2 --     Ph  2  L1 -- C.sub.9 H.sub.19                   438                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Py2 --     Ph23F                                                                             2  L1 -- C.sub.4 H.sub.9                    439                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      --  Ph  --     Py1 2  L1 Ph C.sub.6 H.sub.13                   440                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Py2 --     Ph3F                                                                              2  L1 -- C.sub.7 H.sub.15                   441                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Cy  --     Ph  8  L2 -- C.sub.4 H.sub.8 OC.sub.4                                                      F.sub.9                            442                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      --  Np  --     Ph  2  L1 -- C.sub.14 H.sub.29                  443                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Cy  --CH═CH--                                                                        Ph  4  L1 -- C.sub.10 H.sub.21                  444                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Ep2 --COO--                                                                              Ph  3  L1 -- C.sub.6 H.sub.13                   445                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Pa  --     Ph  7  L1 -- C.sub.8 H.sub.17                   446                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Ph  --     Pd  2  L1 Ph C.sub.6 H.sub.13                   447                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Py2 --     Ph  2  L1 -- (CH.sub.2).sub.6 CH═CH.sub.                                               2                                  448                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Ph  --     Tn  2  L1 -- C.sub.9 H.sub.19                   449                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      --  Py2 --     Ph  6  L2 -- C.sub.6 H.sub.13                   450                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Gp2 --     Ph  2  L1 -- C.sub.8 H.sub.17                   451                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      --  Tz2 --     Ph  2  L1 Ph H                                  452                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Td  --     Ph  9  L1 -- C.sub.8 H.sub.17                   453                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Dx2 --     Ph  2  L1 -- C.sub.7 H.sub.15                   454                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      --  Bta2                                                                              --     Ph  2  L1 -- C.sub.10 H.sub.21                  455                                                                              C.sub.4 F.sub.9 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 O                                   --  Btb2                                                                              --     Ph  4  L1 -- C.sub.6 H.sub.13                   456                                                                              C.sub.6 F.sub.13 CH.sub.2 O                                                               --  Py2 --     Ph  2  L1 -- C.sub.6 H.sub.13                   457                                                                              C.sub.5 F.sub.11 CH.sub.2 O                                                               --  Ph  --     Py1 4  L2 -- C.sub.14 H.sub.29                  458                                                                              C.sub.6 F.sub.13 CH.sub.2 O                                                               --  Np  --COO--                                                                              Ph  2  L1 Ph C.sub.7 H.sub.15                   459                                                                              C.sub.8 F.sub.17 CH.sub.2 O                                                               --  Py1 --     Ph  5  L1 -- C.sub.10 H.sub.21                  460                                                                              C.sub.10 F.sub.21 CH.sub.2 O                                                              --  Py2 --     Ph  2  L1 -- C.sub.6 H.sub.13                   461                                                                              C.sub.4 F.sub.9 CH.sub.2 O                                                                --  Gp1 --     Pr1 2  L1 -- C.sub.12 H.sub.25                  462                                                                              C.sub.3 F.sub.7 CH.sub.2 O                                                                --  Pr2 --     Ph  6  L2 Ph OCH.sub.2 CF.sub.2 OC.sub.2                                                   F.sub.5                            463                                                                              C.sub.6 F.sub.13 CH.sub.2 O                                                               --  Py1 --     Py1 2  L1 -- C.sub.8 H.sub.17                   464                                                                              C.sub.6 F.sub.13 CH.sub.2 O                                                               --  Ph  --     Ph  8  L2 -- C.sub.6 H.sub.13                   465                                                                              C.sub.9 F.sub.19 CH.sub.2 O                                                               --  Ph  --COO--                                                                              Ph  2  L1 -- C.sub.4 H.sub.9                    466                                                                              C.sub.8 F.sub.17 CH.sub.2 O                                                               --  Ph  --     Cy  2  L1 Ph H                                  467                                                                              C.sub.8 H.sub.17                                                                          --  Py2 --     Ph  2  L1 Ph CF.sub.3                           468                                                                              C.sub.5 H.sub.11                                                                          --  Py2 --     Ph2F                                                                              4  L2 Ph CF.sub.3                           469                                                                              C.sub.6 H.sub.13                                                                          --  Py2 --     Ph  2  L1 -- CF.sub.3                           470                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      --  Ph  --     Ph  2  L1 -- CF.sub.3                           471                                                                              C.sub.8 F.sub.17 CH.sub.2 O                                                               --  Ph  --     Ph  6  L2 -- CF.sub.3                           472                                                                              C.sub.6 H.sub.13 O                                                                        --  Ph  --     Ph  4  L2 Ph F                                  473                                                                              CH.sub.2 ═CH(CH.sub.2).sub.3 O                                                        --  Ph  --     Ph  6  L2 Ph F                                  474                                                                              C.sub.9 H.sub.19                                                                          --  Ph  --     Ph  7  L2 Ph F                                  475                                                                              C.sub.5 H.sub.11 O                                                                        --  Ph  --     Ph  4  L2 Ph CN                                 476                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  8  L2 -- CH.sub.3                           477                                                                              C.sub.2 F.sub.5 OCF.sub.2 CH.sub.2 O                                                      Pr2 Ph  --     Ph  3  L2 -- CN                                 478                                                                              C.sub.8 H.sub.17                                                                          --  Id1 --     Ph  2  L1 Ph OCH.sub.3                          479                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  2  L1 -- (CH.sub.2).sub.6 CH═CH.sub.                                               2                                  480                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  2  L1 -- CH.sub.2 OC.sub.6 H.sub.13         481                                                                              C.sub.8 H.sub.17                                                                          --  Ep2 --     Ph  2  L1 -- C.sub.6 H.sub.13                   482                                                                              C.sub.8 H.sub.17                                                                          --  Gp2 --     Ph  4  L1 -- C.sub.6 H.sub.13                   483                                                                              C.sub.10 H.sub.21 O                                                                       --  Py2 --     Ph  2  L1 -- C.sub.6 H.sub.13                   484                                                                              C.sub.10 H.sub.21 O                                                                       --  Py2 --     Ph  2  L1 -- C.sub.5 H.sub.11                   485                                                                              C.sub.10 H.sub.21 O                                                                       --  Py2 --     Ph  2  L1 -- C.sub.8 H.sub.17                   486                                                                              C.sub.8 H.sub.17                                                                          --  Py2 --     Ph  2  L1 -- C.sub.8 H.sub.17                   487                                                                              C.sub.8 H.sub.17                                                                          --  Py2 --     Ph  2  L1 -- C.sub.6 H.sub.13                   488                                                                              C.sub.8 H.sub.17                                                                          --  Py2 --     Ph  2  L1 -- C.sub.5 H.sub.11                   489                                                                              C.sub.10 H.sub.21 O                                                                       --  Py2 --     Ph  4  L1 -- C.sub.6 H.sub.13                   490                                                                              C.sub.10 H.sub.21 O                                                                       --  Py2 --     Ph  5  L1 -- C.sub.6 H.sub.13                   491                                                                              La1(0,6)CH.sub.2 CH.sub.2                                                                 --  Py2 --     Ph  2  L1 -- C.sub.6 H.sub.13                   492                                                                              La2(0,6)CH.sub.2 O                                                                        --  Ph  --     Ph  4  L1 -- C.sub.6 H.sub.13                   493                                                                              Lc1(0,5)    --  Ph  --     Ph  2  L1 -- C.sub.7 H.sub.15                   494                                                                              Lc2(1,1)OCO --  Ph  --     Ph  5  L1 -- C.sub.10 H.sub.21                  495                                                                              P1a-OCO     --  Ph  --     Ph  2  L2 -- C.sub.6 H.sub.13                   496                                                                              Thf(0)-COO  --  Ph  --     Ph  2  L1 -- C.sub.10 H.sub.21                  497                                                                              Dp(2)-CH.sub.2 O                                                                          --  Ph  --     Ph  6  L2 -- C.sub.10 H.sub.21                  498                                                                              Ox(3)-CH.sub.2 O                                                                          --  Ph  --     Ph  2  L1 -- C.sub.8 H.sub.17                   499                                                                              Ox(4)-COO   --  Ph  --     Ph  8  L2 -- C.sub.6 H.sub.13                   500                                                                              La1(0,6)    --  Ph  --     Ph  2  L1 -- C.sub.4 H.sub.9                    501                                                                              C.sub.10 H.sub.21 O                                                                       --  Py2 --     Ph  2  L1 -- CH.sub.2 OC.sub.6 H.sub.13         502                                                                              La1(0,5)-(CH2)4                                                                           --  Py2 --     Ph  4  L1 -- C.sub.6 H.sub.13                   503                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  2  L1 -- C.sub.3 H.sub.7                    504                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  4  L1 -- C.sub.6 H.sub.13                   505                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  3  L1 -- C.sub.6 H.sub.13                   506                                                                              C.sub.10 H.sub.21                                                                         --  Py2 --     Ph  4  L2 -- C.sub.6 H.sub.13                   507                                                                              C.sub.5 H.sub.11                                                                          --  Cy  --     Ph  4  L2 -- C.sub.6 H.sub.13                   508                                                                              C.sub.10 H.sub.21                                                                         --  Ph  --     Py1 4  L2 -- C.sub.6 H.sub.13                   __________________________________________________________________________

According to the present invention, there is also provided compoundsrepresented by the following general formula (II) as compounds relatingto the compounds represented by general formula (I):

    CH.sub.2 ═CH--(CH.sub.2).sub.p '--L'--R.sub.2          (II)

where p' is an integer from 0 to 18, L' is optically active4-butanolyde-2,4-diyl and R₂ is R₂ is F, CN or straight chain, branchedor cyclic alkyl group (one or more --CH₂ -- in the alkyl group may bereplaced by --O--, --S--, --CO--, --CH (CN)--, --CH═CH-- or --C.tbd.C--under condition that hetero atoms do not position adjacent) which has 3to 30 carbon atoms and which can be substituted.

In the optically active compound represented by general formula (II), itis preferable that p' is an integer from 0 to 10, and more preferably aninteger from 0 to 4, and most preferably an integer 0, 2 or 4.

L' is preferably 4-butanolyde-2,4-diyl and R2 is preferably a straightchain alkyl group having 4 to 10 carbon atoms.

In the viewpoints of easily performing the preparing process andobtaining stability, it is preferable that L' in the compoundrepresented by general formula (II) is 4-butanolyde-2,4-diyl and R₂ is astraight chain hexyl group.

The optically active compound represented by general formula (II) isadvantageous to serve as an intermediate material for preparing theoptically active compound represented by general formula (I) in a casewhere L' is 4-butanolyde-2,4-diyl and as well as R₂ is --C₆ H₁₃ --.Furthermore, it is an effective compound to serve as an intermediatematerial for preparing a functional material and any of a variety ofoptically active materials (refer to the foregoing preparing methods Bto D).

Schematic constitutional formula of the optically active compoundrepresented by general formula (II) is shown in Table 2.

    CH.sub.2 ═CH.sub.2 (CH.sub.2).sub.p '--L'--R.sub.2     (II)

                  TABLE 2                                                         ______________________________________                                        No.      P'            L'    R2                                               ______________________________________                                        509      0             L1    C.sub.6 H.sub.13                                 510      1             L1    C.sub.6 H.sub.13                                 511      2             L1    C.sub.6 H.sub.13                                 512      3             L1    C.sub.6 H.sub.13                                 513      4             L1    C.sub.6 H.sub.13                                 514      5             L1    C.sub.6 H.sub.13                                 515      6             L1    C.sub.6 H.sub.13                                 516      7             L1    C.sub.6 H.sub.13                                 517      8             L1    C.sub.6 H.sub.13                                 518      9             L1    C.sub.6 H.sub.13                                 519      10            L1    C.sub.6 H.sub.13                                 520      0             L2    C.sub.6 H.sub.13                                 521      1             L2    C.sub.6 H.sub.13                                 522      2             L2    C.sub.6 H.sub.13                                 523      3             L2    C.sub.6 H.sub.13                                 524      4             L2    C.sub.6 H.sub.13                                 525      5             L2    C.sub.6 H.sub.13                                 526      6             L2    C.sub.6 H.sub.13                                 527      7             L2    C.sub.6 H.sub.13                                 528      8             L2    C.sub.6 H.sub.13                                 529      9             L2    C.sub.6 H.sub.13                                 530      10            L2    C.sub.6 H.sub.13                                 531      0             L1    C.sub.3 H.sub.7                                  532      1             L1    C.sub.3 H.sub.7                                  533      2             L1    C.sub.3 H.sub.7                                  534      3             L1    C.sub.3 H.sub.7                                  535      4             L1    C.sub.3 H.sub.7                                  536      5             L1    C.sub.3 H.sub.7                                  537      6             L1    C.sub.3 H.sub.7                                  538      7             L1    C.sub.3 H.sub.7                                  539      8             L1    C.sub.3 H.sub.7                                  540      9             L1    C.sub.3 H.sub.7                                  541      10            L1    C.sub.3 H.sub.7                                  542      0             L2    C.sub.3 H.sub.7                                  543      1             L2    C.sub.3 H.sub.7                                  544      2             L2    C.sub.3 H.sub.7                                  545      3             L2    C.sub.3 H.sub.7                                  546      4             L2    C.sub.3 H.sub.7                                  547      5             L2    C.sub.3 H.sub.7                                  548      6             L2    C.sub.3 H.sub.7                                  549      7             L2    C.sub.3 H.sub.7                                  550      8             L2    C.sub.3 H.sub.7                                  551      9             L2    C.sub.3 H.sub.7                                  552      10            L2    C.sub.3 H.sub.7                                  553      0             L1    C.sub.4 H.sub.9                                  554      1             L1    C.sub.4 H.sub.9                                  555      2             L1    C.sub.4 H.sub.9                                  556      3             L1    C.sub.4 H.sub.9                                  557      4             L1    C.sub.4 H.sub.9                                  558      5             L1    C.sub.4 H.sub.9                                  559      6             L1    C.sub.4 H.sub.9                                  560      7             L1    C.sub.4 H.sub.9                                  561      8             L1    C.sub.4 H.sub.9                                  562      9             L1    C.sub.4 H.sub.9                                  563      10            L1    C.sub.4 H.sub.9                                  564      0             L2    C.sub.4 H.sub.9                                  565      1             L2    C.sub.4 H.sub.9                                  566      2             L2    C.sub.4 H.sub.9                                  567      3             L2    C.sub.4 H.sub.9                                  568      4             L2    C.sub.4 H.sub.9                                  569      5             L2    C.sub.4 H.sub.9                                  570      6             L2    C.sub.4 H.sub.9                                  571      7             L2    C.sub.4 H.sub.9                                  572      8             L2    C.sub.4 H.sub.9                                  573      9             L2    C.sub.4 H.sub.9                                  574      10            L2    C.sub.4 H.sub.9                                  575      0             L1    C.sub.5 H.sub.11                                 576      1             L1    C.sub.5 H.sub.11                                 577      2             L1    C.sub.5 H.sub.11                                 578      3             L1    C.sub.5 H.sub.11                                 579      4             L1    C.sub.5 H.sub.11                                 580      5             L1    C.sub.5 H.sub.11                                 581      6             L1    C.sub.5 H.sub.11                                 582      7             L1    C.sub.5 H.sub.11                                 583      8             L1    C.sub.5 H.sub.11                                 584      9             L1    C.sub.5 H.sub.11                                 585      10            L1    C.sub.5 H.sub.11                                 586      0             L2    C.sub.5 H.sub.11                                 587      1             L2    C.sub.5 H.sub.11                                 588      2             L2    C.sub.5 H.sub.11                                 589      3             L2    C.sub.5 H.sub.11                                 590      4             L2    C.sub.5 H.sub.11                                 591      5             L2    C.sub.5 H.sub.11                                 592      6             L2    C.sub.5 H.sub.11                                 593      7             L2    C.sub.5 H.sub.11                                 594      8             L2    C.sub.5 H.sub.11                                 595      9             L2    C.sub.5 H.sub.11                                 596      10            L2    C.sub.5 H.sub.11                                 597      0             L1    C.sub.7 H.sub.15                                 598      1             L1    C.sub.7 H.sub.15                                 599      2             L1    C.sub.7 H.sub.15                                 600      3             L1    C.sub.7 H.sub.15                                 601      4             L1    C.sub.7 H.sub.15                                 602      5             L1    C.sub.7 H.sub.15                                 603      6             L1    C.sub.7 H.sub.15                                 604      7             L1    C.sub.7 H.sub.15                                 605      8             L1    C.sub.7 H.sub.15                                 606      9             L1    C.sub.7 H.sub.15                                 607      10            L1    C.sub.7 H.sub.15                                 608      0             L2    C.sub.7 H.sub.15                                 609      1             L2    C.sub.7 H.sub.15                                 610      2             L2    C.sub.7 H.sub.15                                 611      3             L2    C.sub.7 H.sub.15                                 612      4             L2    C.sub.7 H.sub.15                                 613      5             L2    C.sub.7 H.sub.15                                 614      6             L2    C.sub.7 H.sub.15                                 615      7             L2    C.sub.7 H.sub.15                                 616      8             L2    C.sub.7 H.sub.15                                 617      9             L2    C.sub.7 H.sub.15                                 618      10            L2    C.sub.7 H.sub.15                                 619      0             L1    C.sub.8 H.sub.17                                 620      1             L1    C.sub.8 H.sub.17                                 621      2             L1    C.sub.8 H.sub.17                                 622      3             L1    C.sub.8 H.sub.17                                 623      4             L1    C.sub.8 H.sub.17                                 624      5             L1    C.sub.8 H.sub.17                                 625      6             L1    C.sub.8 H.sub.17                                 626      7             L1    C.sub.8 H.sub.17                                 627      8             L1    C.sub.8 H.sub.17                                 628      9             L1    C.sub.8 H.sub.17                                 629      10            L1    C.sub.8 H.sub.17                                 630      0             L2    C.sub.8 H.sub.17                                 631      1             L2    C.sub.8 H.sub.17                                 632      2             L2    C.sub.8 H.sub.17                                 633      3             L2    C.sub.8 H.sub.17                                 634      4             L2    C.sub.8 H.sub.17                                 635      5             L2    C.sub.8 H.sub.17                                 636      6             L2    C.sub.8 H.sub.17                                 637      7             L2    C.sub.8 H.sub.17                                 638      8             L2    C.sub.8 H.sub.17                                 639      9             L2    C.sub.8 H.sub.17                                 640      10            L2    C.sub.8 H.sub.17                                 ______________________________________                                    

The liquid crystal composition according to the present invention can beprepared by mixing one or more optically active compounds represented bygeneral formula (I), preferably (I'), and one or more other liquidcrystal compounds (mesomorphic compounds) at an adequate ratio. Thenumber of the other liquid crystal compounds to be used together is 1 to50, preferably 1 to 30, and most preferably 3 to 30.

The "mesomorphic compound" according to the present invention isrequired to be liquid crystal or serve as a preferred component of aliquid crystal composition in the composition.

It is preferable that the liquid crystal composition according to thepresent invention be a chiral smectic liquid crystal composition, and inparticular, be a ferroelectric chiral smectic liquid crystalcomposition.

The "other liquid crystal compound" according to the present inventionmay be any of the following materials disclosed in Japanese PatentLaid-Open No. 4-272989: compounds (III) to (XII), preferably (IIIa) to(XIId), and more preferably (IIIaa) to (XIIdb). Furthermore, any of thefollowing compounds may be employed: compounds (III) to (VI), preferably(IIIa) to (VIf) and more preferably (IIIaa) to (VIfa), in which R'₁and/or R'₂ is --(CH₂)_(E) C_(G) F_(2G+1) (where E is an integer from 0to 10 and G is an integer from 1 to 15), a compound (VII) or (VIII),preferably (VIIa) to (VIIIb) and more preferably (VIIIba) or (VIIIbb) inwhich R'₃ and/or R'₄ is the same, and a compound (IX) to (XII),preferably (IXa) to (XIId) and more preferably (IXba) or (XIIdb) inwhich R'₅ and/or R'₆ is the same. Moreover, the following liquid crystalcompound represented by the following general formulas (XIII) to (XVIII)may be used:

    R'.sub.7 --X'.sub.6 -- Py2!-X'.sub.7 -- Ph!--X'.sub.8 --( PhY'.sub.7 !).sub.N -- Tn!--R'.sub.8                                 (XIII)

    R'.sub.7 --X'.sub.6 -- Py2!- Ph!--OCO-- Ph4F!              (XIV)

    R'.sub.7 --X'.sub.6 -- Py2!- Ph!--OCO-- Ph34F!             (XV)

    R'.sub.7 --( PhY'.sub.7).sub.Q -- Tz1!- PhY'.sub.8 !--X'.sub.7 --( PhY'.sub.9 !).sub.R --( CY!).sub.τ --X'.sub.9 --R'.sub.8(XVI)

    R'.sub.7 -- Bo2!-A'.sub.4 --X'.sub.9 --R'.sub.8            (XVII)

    R'.sub.7 -- Bt2!-A'.sub.4 --X'.sub.9 --R'.sub.8            (XVIII)

where R'₇ and R'₈ are straight or branched alkyl groups having 1 to 18hydrogen atoms or carbon atoms, wherein one or two or more --CH₂ --groups, which are not positioned adjacent may, except the --CH₂ --groups which are directly bonded to X'₆ and X'₉, be replaced by --O--,--CO--, --OCO--, --COO--, --CH (CN)-- or --C (CN) (CH₃).

It is preferable that R'₇ and R'₈ be (i) to (viii). (i) A straight chainalkyl group having 1 to 15 carbon atoms. ##STR6## where p is an integerfrom 0 to 5 and q is an integer from 2 to 11, and which may be opticallyactive. ##STR7## where r is an integer from 0 to 6, s is an integer 0 or1 and t is an integer from 1 to 14, and which may be optically active.##STR8## where w is an integer from 1 to 15, and which may be opticallyactive. ##STR9## where A is an integer from 0 to 2 and B is an integerfrom 1 to 15, and which may be optically active. ##STR10## where C is aninteger from 0 to 2 and D is an integer from 1 to 15, and which may beoptically active.

    --(CH.sub.2).sub.E C.sub.G F.sub.2G+1                      (vii)

where E is an integer from 0 to 10 and G is an integer from 1 to 15.

    --H                                                        (viii)

wherein N, Q, R and T respective are integer 0 or 1, Y'₇, Y'₈ and Y'₉respective are H or F, A'₄ is Ph or Np, X'₆ and X'₉ respectively aresingle bonds, --COO--, --OCO-- or --O--, X'₇ and X'₈ are single bonds,--COO--, --OCO--, --CH₂ O-- or --OCH₂ --.

As a preferred compound of (XIII), the following compound (XIIIa) isexemplified:

    R'.sub.7 --X'.sub.6 -- Py2!- Ph!--OCO-- Tn!--R'.sub.8      (XIIIa)

As a preferred compound of (XVI), the following compounds (XVIa) and(XVIb) are exemplified:

    R'.sub.7 -- Tz1!- Ph!--X'.sub.9 --R'.sub.8                 (XVIa)

    R'.sub.7 -- PhY'.sub.7 !-- Tz1!- PhY'.sub.8 !--X'.sub.9 --R'.sub.8(XVIb)

As a preferred compound of (XVII), the following compounds (XVIIa) and(XVIIb) are exemplified:

    R'.sub.7 -- Boa2!- Ph!--O--R'.sub.8                        (XVIIa)

    R'.sub.7 -- Boa2!- Np!--O--R'.sub.8                        (XVIIb)

As a preferred compound of (XVIII), the following compounds (XVIIIa) and(XVIIIc) are exemplified:

    R'.sub.7 -- Btb2!- Ph!--R'.sub.8                           (XVIIIa)

    R'.sub.7 -- Btb2!- Ph!--O--R'.sub.8                        (XVIIIb)

    R'.sub.7 -- Btb2!- NP!--O--R'.sub.8                        (XVIIIc)

As preferred compounds of (XVIa) and (XVIb), the following compounds(XVIaa) to (XVIbc) are exemplified:

    R'.sub.7 -- Tz1!- Ph!--O--R'.sub.8                         (XVIaa)

    R'.sub.7 -- Ph!-- Tz1!- Ph!R'.sub.8                        (XVIba)

    R'.sub.7 -- Ph!-- Tz1!- Ph!--O--R'.sub.8                   (XVIbb)

    R'.sub.7 -- Ph!-- Tz1!- Ph!--OCO--R'.sub.8                 (XVIbc)

wherein abbreviated forms Ph, Py2, Tn, Tz1, Cy, Boa2 and Btb2 aredefined similarly to the foregoing definitions and other abbreviatedforms represent the following groups: ##STR11##

In a case where the optically active compound according to the presentinvention and one or more kinds of the foregoing liquid crystalcompounds or the liquid crystal compositions are mixed, it is preferablethat the ratio of the optically active compound according to the presentinvention in the liquid crystal composition obtained by mixing be 1 wt %to 80 wt %. To put into practice the chiral smectic liquid crystaldevice, in particular, the ferroelectric liquid crystal device, amultiplicity of conditions, such as the liquid crystal characteristic,high speed response, high contrast and uniform switching, must be met ina wide temperature range. However, any single compound cannot satisfyall of the foregoing conditions. Therefore, multiple kinds of compoundsrespectively having individual advantage are usually used to prepare theliquid crystal composition. From the foregoing viewpoint, it ispreferable that the ratio of the optically active compound according tothe present invention in the liquid crystal composition be 1 wt % to 60wt %. To cause the characteristics of the other liquid crystal compoundsto be exhibited, it is preferable that the ratio be 1 wt % to 40 wt %.If the ratio is lower than 1 wt %, the effect of the compound accordingto the present invention is unsatisfactory.

It is preferable that two or more kinds of the optically activecompounds according to the present invention be used. In this case, theratio of the mixture of the two or more kinds of the optically activecompounds according to the present invention in the liquid crystalcomposition prepared by mixing is 1 wt % to 80 wt %. In the viewpoint ofpreparing the liquid crystal composition composed of multiple kinds ofcompounds, it is preferable that the ratio be 1 wt % to 60 wt %, andmore preferably 1 wt % to 40 wt % to cause the characteristics of theother liquid crystal compounds to exhibit.

It is preferable that the chiral smectic phase liquid crystal layer, inparticular, the liquid crystal layer of the liquid crystal deviceaccording to the present invention be subjected to the processes suchthat the liquid crystal composition prepared as described above is, in avacuum state, heated to an isotropic liquid temperature; it is enclosedin a cell for the device; it is gradually cooled to form the liquidcrystal layer; and then the temperature is returned to room temperature.

FIG. 1 is schematic cross sectional view which illustrates an example ofthe liquid crystal device having the chiral smectic phase liquid crystallayer, in particular, a ferroelectric liquid crystal liquid crystallayer according to the present invention to describe the structure ofthe liquid crystal device. Referring to FIG. 1, reference numeral 1represents a liquid crystal layer, 2 represents a glass substrate, 3represents a transparent electrode, 4 represents an insulatingorientation control layer, 5 represents a spacer, 6 represents a leadwire, 7 represents a power source, 8 represents a polarizing plate and 9represents a light source.

The two glass plates 2 are coated with the transparent electrodes 3 madeof thin films of In₂ O₃, SnO₂ or ITO (Indium Tin Oxide). Then, polymerthin films, such as polyimide, are rubbed with gauze or acetate fillingcloth or the like so that the insulating orientation control layer 4 isformed to orient the liquid crystal in the rubbing direction.

The insulating orientation control layer 4 may be composed of two layersconsisting of: an inorganic insulating layer, the insulating material ofwhich is any of the following materials: a silicon nitride, a siliconcarbide containing hydrogen, a silicon oxide, a boron nitride, a boronnitride containing hydrogen, a cerium oxide, an aluminum oxide, azirconium oxide, a titanium oxide and magnesium fluoride; and aorientation control layer made of an organic insulating material, suchas polyvinyl alcohol, polyimide, polyamideimide, polyester imide,polyparaxylene, polyester, polycarbonate, polyvinyl acetal, polyvinylchloride, polyvinyl acetate, polyamide, polystyrene, cellulose resin,melamine resin, urea resin, acryl resin or photoresist resin. As analternative to this, the insulating orientation control layer 4 may beformed solely by an insulating orientation control layer mainly composedof inorganic substances or an insulating orientation control layermainly composed of organic substances. If the insulating orientationcontrol layer is mainly made of inorganic substances, it can be formedby an evaporating method. If it is mainly made of organic substances,the insulating orientation control layer can be formed by using asolution in which the organic insulating substances are dissolved or asolution of the precursor of the organic insulating substances (in aquantity of 0.1 wt % to 20 wt % of the solvent) and by hardening thematerial under a predetermined hardening condition (for example, withheat) by a spinner coating method, a dipping coating method, a screenprinting method, a spray coating method or a roll coating method.

The thickness of the insulating orientation control layer 4 is usually10 Å to 1 μm, preferably 10 Å to 3000 Å, and most preferably 10 Å to1000 Å. The two glass substrates 2 are positioned at arbitrary intervalby the spacer 5. For example, silica beads or alumina beads each havinga predetermined diameter are used as the spacer 5 to be held between thetwo glass substrates 2. Then, a sealing material, for example, an epoxybond is used to seal the peripheral portion. As the spacer, a polymerfilm or glass fiber may be used. The foregoing chiral smectic liquidcrystal composition is enclosed between the two glass substrates 2.

The liquid crystal layer 1, in which the liquid crystal has beenenclosed, usually has a thickness of 0.5 μm to 20 μm, and preferably 1μm to 5 μm.

The transparent electrodes 3 are connected to the external power source7 through lead wires 6. The polarizing plates 8 are applied on the twoexternal sides of the glass plates 2. Since the liquid crystal deviceshown in FIG. 1 is a transmissive type device, the light source 9 isprovided. FIG. 2 is a schematic view of the cell to explain theoperation of the liquid crystal device. Reference numerals 21a and 21brepresent substrates (glass plates) respectively coated with thin filmsmade of In₂ O₃, SnO₂ or ITO (Indium Tin Oxide). Liquid crystal of phaseS*C or S*H oriented such that their liquid crystal molecule layers 22are perpendicular to the surfaces of the glass plates 21a and 21b isenclosed between the substrates 21a and 21b. Bold lines 23 represent theliquid crystal molecules, the liquid crystal molecules 23 each havingdipole moment (P ⊥) 24. When voltage, the threshold of which is largerthan a predetermined value, is applied between the substrates 21a and21b, the spiral structures of the liquid crystal molecules 23 areuntied. Thus, the direction of orientation of the liquid crystalmolecules 23 can be changed such that all dipole moments (P ⊥) 24 facethe direction of the electric field. The liquid crystal molecule 23 hasan elongated shape in which its longer axial direction and a shorteraxial direction have anisotropy of the refraction factor. Therefore, itcan easily be understand that placing of polarizers crossed-Nicol eachother on the upper and lower surfaces of the glass surface enables aliquid crystal optical modulating device to be constituted, the opticalcharacteristic of which is changed based on the polarity of the appliedvoltage.

The thickness of the liquid crystal cell for use preferably in theoptical modulating device according to the present invention can bereduced satisfactorily (for example, 10 μm or thinner). As the liquidcrystal layer is thinned as described above, the spiral structures ofthe liquid crystal molecules are untied as shown in FIG. 3 even if noelectric field is applied. As a result, the dipole moment Pa or Pb isbrought into an upward direction 34a or a downward direction 34b. Whenan electric field Ea or Eb larger than a predetermined threshold is, asshown in FIG. 3, applied to a cell of the foregoing type by voltageapplying means 31a and 31b, the dipole moments change their direction tothe upward direction 34a or the downward direction 34b to correspond tothe electric field vector. Correspondently, the liquid crystal moleculesare oriented to a first stable state 33a or a second stable state 33b.

Use of the ferroelectric liquid crystal device as the optical modulatingdevice enables two advantages as described above. The first advantage isthat a very first response speed can be obtained. The second advantageis that the liquid crystal molecules have the bistability. The secondadvantage will now be described with reference to FIG. 3. When theelectric field Ea is applied, the direction of the liquid crystalmolecules are changed so as to be oriented into the second stable state33b. Even if the electric field is turned off, the liquid crystalmolecules are maintained at the foregoing state. If the applied electricfield Ea or Eb does not exceed a predetermined threshold, the previousstate of orientation is maintained.

FIG. 5 illustrates operation waveforms according to the presentinvention. Referring to FIG. 5(A), symbols S_(S) represent selectedscanning waveforms to be applied to selected scanning lines, S_(N)represent non-selected scanning waveforms to be applied to non-selectedscanning lines, I_(S) represent selected information waveform (black) tobe applied to selected data lines and I_(N) represent non-selectedinformation signal (white) to be applied to non-selected data lines.Referring to FIG. 5(A), (I_(S) -S_(S)) and (I_(N) -S_(S)) representvoltage waveforms to be applied to pixels on the selected scanninglines. Pixels applied with voltage (I_(S) -S_(S)) are brought into ablack display state, while pixels applied with voltage (I_(N) -S_(S))are brought into a white display state.

FIG. 5(B) illustrates time-sequential waveforms realized when displayshown in FIG. 6 is performed with the operation waveforms shown in FIG.5(A). In the example of the operation shown in FIG. 5, shortest applyingtime Δt, in which the pixel on the selected scanning line is appliedwith monopole voltage, corresponds to the time of writing phase t₂. Thetime t₁ for clearing one line is set to 2Δt. The values of therespective parameters V_(S), V_(I) and Δt of the operation waveformsshown in FIG. 5 are determined depending upon the switchingcharacteristic of the employed liquid crystal material. In thisembodiment, determination is fixed such that V_(I) /(V_(I) +V_(S))=1/3.Although the range of the adequate operating voltage can be widened byraising the bias ratio, the raise of the bias ratio causes the amplitudeof the information signal to be widened and thus the image qualitydeteriorates such that flickers take place and the contrast is lowered.Investigations performed by the inventors of the present inventionresulted in that the practical bias ratio is 1/3 to 1/4.

The liquid crystal device according to the present invention may beadequately combined with another device or a circuit to constitute avariety of liquid crystal devices.

In particular, the liquid crystal device according to the presentinvention is used in a display panel portion and a communicationsynchronizing means is provided so that a liquid crystal displayapparatus is realized, the communication synchronizing means beingadapted to a data format composed of image information having thescanning address information shown in FIGS. 7 and 8 and a SYNC signal.

Referring to FIGS. 7 and 8, reference numeral 101 represents a liquidcrystal display apparatus, 102 represents a graphic controller, 103represents a display panel, 104 represents a scanning line operatingcircuit, 105 represents an information line operating circuit, 106represents a decoder, 107 represents a scanning signal generatingcircuit, 108 represents a shift register, 109 represents a line memory,110 represents an information signal generating circuit, 111 representsan operation control circuit, 112 represents a GCPU, 113 represents ahost CPU and 114 represents a VRAM.

Image information is generated by the graphic controller 102 providedfor the apparatus body, the image information being transferred to thedisplay panel 103 by a signal transferring means shown in FIGS. 7 and 8.The graphic controller 102 controls image information and communicationbetween the host CPU 113 and the liquid crystal display apparatus 101depending upon the CPU (central processing unit, hereinafter abbreviatedto a "GCPU 112") and the VARM (an image information storage memory) 114.The control method according to the present invention is realized mainlyon the graphic controller 102. Note that a light source is disposed onthe reverse side of the display panel 103.

Examples of the present invention will now be described in detail. Thepresent invention is not limited to the examples below.

EXAMPLE 1

Preparation of optically active 2- 2-{4-(4-methoxyphenyl)phenyl}ethyl!-4-hexyl-4-butanolyde (Example Compound No. 4)

(1) Preparation of 2-(4-bromophenyl) ethylbenzylether

6.12 g (30.4 mmol) of 4-bromophenthylalcohol, 1.34 g (33.4 mmol) of 60%sodium hydride and 23 ml of tetrahydrofuran (THF) were injected. Then, amixture solution of 7.84 g (62.0 mol) of benzylchloride and 10 ml of THFwere dripped, and the materials were stirred for 2.5 hours while beingheated at 80° C. After reactions had been completed, the materials werecooled, and water was added, extraction with toluene, cleaning wit waterand drying were performed. The solvent was removed by filtration, andthen refining was performed with a silica gel column chromatography(developing solvent: toluene/hexane=1/3) so that 7.0 g of2-(4-bromophenyl) ethylbenzylether was obtained (yield 79%).

(2) Preparation of 2-{4-(4-methoxyphenyl) phenyl}ethylbenzylether

1.57 g (10.3 mmol) of 4-methoxyphenyl malonic acid, 3.0 g (10.3 mmol) of2-(4-bromophenyl) ethylbenzylether, 0.38 g of tetrakis(triphenylphosphine) palladium, 15 ml of 2M-sodium carbonate solution,15 ml of toluene and 10 ml of ethanol were heated at 80° C. for 4 hoursunder presence of nitrogen. After reactions had been completed,extraction with toluene was performed. Then, the extracted solution wasdried with anhydrous sodium sulfate. The solvent was removed byfiltration, and then refining was performed with a silica gel columnchromatography (developing solvent: toluene) and by recrystallization(ethanol) so that 2.63 g of 2-{4-(4-methoxyphenyl)phenyl}ethylbenzylether was obtained (yield 80%).

(3) Preparation of 2-{4-(4-methoxyphenyl) phenyl}ethanol

2,59 g (7.85 mol) of 2-{4-(4-methoxyphenyl) phenyl}ethylbenzylether, 0.4g of 5% palladium activated carbon, 70 ml of ethanol and 6 ml of dioxanewere injected and stirred at room temperature for 7 hours under presenceof hydrogen. After the reactions had been completed, the catalyst wasremoved by tuck filtration and the solvent was removed by filtration sothat 1.64 g of 2-{4-(4-methoxyphenyl) phenyl}ethanol was obtained (yield92%).

(4) Preparation of 4-toluenesulfonic acid 2-{4-(4-methoxyphenyl)phenyl}ethyl

1.64 g (7.18 mmol) of 2-{4-(4-methoxyphenyl)phenyl}ethanol, 1.44 g (7.54mmol) of 4-toluenesulfonic acid chloride, 3.20 g (40.5 mmol) of pyridineand 5 ml of dichloromethane were stirred at room temperature for 5hours. After the reactions had been completed, cooling was performed, 10ml of 6M-hydrochloric acid was added, extraction with toluene wasperformed, and the extracted solution was dried with anhydrous sodiumsulfate. After the solvent had been removed by filtration, refining wasperformed with a silica gel column chromatography (developing solvent:toluene) so that 2.37 g of 4-toluenesulfonic acid2-{4-(4-methoxyphenyl)phenyl}ethyl was obtained (yield 86%).

(5) Preparation of 2- 2-{4-(4-methoxyphenyl) phenyl}ethyl!diethylmalonate

0.29 g (7.3 mmol) of 60% sodium hydrate and 1 ml ofN,N-dimethylformamide (DMF) were injected, and mixture solution of 1.07g (6.7 mol) of dimethyl malonate and 3 ml of DMF were dripped to theforegoing materials. Stirring at room temperature was performed for 15minutes, and then mixed solution of 2.30 g (6.01 mmol) of 4-toluenesulfonic acid 2-{4-(4-methoxyphenyl) phenyl}ethyl and 5 mol of DMF wasdripped, and then heating and stirring at 100° C. were performed for 6hours. After the reactions had been completed, cooling was performed,water was added and extraction with toluene was performed. Then,cleaning with water and drying were performed. After the solvent wasremoved by filtration, refining was performed with a silica gel columnchromatography (developing solvent: toluene/ethyl acetate=10/1! so that1.35 g of 2- 2-{4-(4-methoxyphenyl)phenyl}ethyl!diethyl malonate wasobtained.

(6) Preparation of optically active 2- 2-{4-(4-methoxyphenyl)phenyl}ethyl!-4-hexyl-4-butanolyde

0.60 g (1.62 mmol) of 2- 2-{4-(4-methoxyphenyl)phenyl}ethyl!diethylmalonate, 0.20 g (1.78 mmol) of t-butoxy potassium and 5 ml of t-butanolwere injected. Then, mixed solution of 0.21 g (1.62 mmol) of opticallyactive 1,2-epoxyoctane and 2 ml of t-butanol was dripped, and thenheating and stirring at 90° C. were performed for 4 hours. After thereactions had been completed, 6M-hydrochloric acid was added so that thepH was made to be 1, and extraction with ethyl acetate was performed.After the extracted solution was dried, the solvent was removed byfiltration. Then, refining was performed with a silica gel columnchromatography (developing solvent: toluene/ethyl acetate=20/1) and byrecrystallization (toluene/methanol) so that 0.20 g of optically active2- 2-{4-(4-methoxyphenyl) phenyl}ethyl!-4-hexyl-4-butanolyde wasobtained (yield 32% and melting point 134.8° C.).

EXAMPLE 2

Preparation of optically active 2- 4-{4-(3-fluorononyloxy)phenyl}phenyl!ethyl-4-hexyl-4-butanolyde (Example Compound No. 5)

(1) Preparation of optically active 2-{4-(4-hydroxyphenyl)phenyl}ethyl-4-hexyl-4-butanolyde

0.38 g (1.0 mmol) of optically active 2-{4-(4-methoxyphenyl)phenyl}ethyl-4-hexyl-4-butanolyde and 6 ml of dichloromethane werecooled to -80° C. Then, mixed solution of 0.15 g (1.2 mmol) of borontribromide and 3 ml of dichloromethane was dripped. Then, stirring wasperformed at room temperature for 15 hours, and 10 ml of water wasadded, and extraction with ethyl acetate was performed. The extractedsolution was cleaned with solution of sodium hydrogen carbonate, andthen it was dried with anhydrous sodium sulfate. After the solvent wasremoved by filtration, refining was performed with a silica gel columnchromatography (developing solvent: toluene/ethyl acetate=10/1) and byrecrystallization (toluene/hexane) so that 0.30 g of optically active2-{4-(4-hydroxyphenyl) phenyl}ethyl-4-hexyl-4-butanolyde was obtained(yield 82%).

(2) Preparation of optically active 2- 4-{4-(3-fluorononyloxy)phenyl}phenyl!ethyl-4-hexyl-4-butanolyde

0.033 g (0.83 mmol) of 60% sodium hydrate and 2 ml of DMF were injected,and a mixed solution of 0.29 g (0.79 mol) of optically active2-{4-(4-hydroxyphenyl) phenyl}ethyl-4-hexyl-4-butanolyde and 3 ml of DMFwas dripped. Stirring was performed at room temperature for 15 minutes,and then a mixed solution of 0.26 g (0.82 mmol) of 4-toluene sulfonicacid 3-fluorononyl and 2 ml of DMF was dripped. Then, heating andstirring at 60° C. were performed for one hour. After the reactions hadbeen completed, cooling was performed, water and methanol were added.Then, precipitated crystal was filtered. The obtained crystal wascleaned with water and methanol. Then, refining was performed with asilica gel column chromatography (developing solvent: toluene/ethylacetate=10/1) and by recrystallization so that 0.32 g of 2-4-{4-(3-fluorononyloxy) phenyl}phenyl!ethyl-4-hexy-4-butanolyde wasobtained (yield 80% and melting point 129.7° C.).

EXAMPLE 3

Preparation of optically active 2- 2-{4-(2-octylindane-5-yl)phenyl}ethyl!-4-octyl-4-butanolyde (Example Compound No. 47)

(1) Preparation of 2-{4-(2-octylindane-5-yl) phenyl}ethanol

2.74 g (10.0 mmol) of 2-octylindane-5-boronic acid, 2.0 g (10.0 mmol) of2-(4-bromophenyl) ethanol, 0.38 g of tetrakis (triphenylphosphine)palladium, 15 ml of 2M-sodium carbonate solution, 15 ml of toluene and10 ml of ethanol were heated at 80° C. for 6 hours under presence ofnitrogen. After reactions had been completed, extraction with toluenewas performed. Then, the extracted solution was dried with anhydroussodium sulfate. The solvent was removed by filtration, and then refiningwas performed by re-crystallization (hexane/ethanol) so that 2.40 g of2-{4-(2-octylindane-5-yl) phenyl}ethanol was obtained (yield 68%).

(2) Preparation of 4-toluene sulfonic acid 2-{4-(2-octylindane-5-yl)phenyl}ethyl

2.40 g (6.85 mmol) of 2-{4-(2-octylindane-5-yl) phenyl}ethanol, 1.31 g(6.85 mmol) of 4-toluenesulfonic acid chloride and 3.20 g (40.5 mmol) ofpyridine were stirred at room temperature for 3 hours. After thereactions had been completed, cooling was performed, 10 ml of6M-hydrochloric acid was added, extraction with toluene was performed,and the extracted solution was dried with anhydrous sodium sulfate.After the solvent had been removed by filtration, refining was performedwith a silica gel column chromatography (developing solvent: toluene) sothat 2.70 g of 4-toluene sulfonic acid 2-{4-(2-octylindane-5-yl)phenyl}ethyl was obtained (yield 78%).

(3) Preparation of 2- 2-{4-(2-octylindane-5-yl) phenyl}ethyl!diethylmalonate

0.23 g (5.67 mmol) of 60% sodium hydrate and 1 ml of DMF were injected,and mixture solution of 0.91 g (5.67 mol) of dimethyl malonate and 3 mlof DMF were dripped to the foregoing materials. Stirring at roomtemperature was performed for 15 minutes, and then mixed solution of2.60 g (5.15 mmol) of 4-toluene sulfonic acid2-{4-(2-octylindane-5-yl)phenyl}ethyl and 5 ml of DMF was dripped, andthen heating and stirring at 90° C. were performed for 4 hours. Afterthe reactions had been completed, cooling was performed, water was addedand extraction with toluene was performed. Then, cleaning with water anddrying were performed. After the solvent was removed by filtration,refining was performed with a silica gel column chromatography(developing solvent: toluene/ethyl acetate=10/1! so that 1.52 g of 2-2-{4-(2-octylindane-5-yl) phenyl}ethyl!diethyl malonate was obtained(yield 60%).

(4) Preparation of optically active 2- 2-{4-(2-octylindane-5-yl)phenyl}ethyl!-4-octyl-4-butanolyde

0.70 g (1.40 mmol) of 2- 2-{4-(2-octylindane-5-yl) phenyl}ethyl!diethylmalonate, 0.17 g (1.56 mmol) of t-butoxy potassium and 8 ml of t-butanolwere injected. Then, mixed solution of 0.22 g (1.42 mmol) of1,2-epoxydecane and 4 ml of t-butanol was dripped, and then heating andstirring at 90° C. were performed for 8 hours. After the reactions hadbeen completed, 6M-hydrochloric acid was added so that the pH was madeto be 1, and extraction with ethyl acetate was performed. After theextracted solution was dried, the solvent was removed by filtration.Then, refining was performed with a silica gel column chromatography(developing,solvent: toluene/ethyl acetate=20/1) and byrecrystallization (toluene/methanol) so that 0.30 g of optically active2- 2-{4-(2-octylindane-5-yl) phenyl}ethyl!-4-octyl-4-butanolyde wasobtained (yield 40%).

Phase Transition Temperature (°C.) ##STR12##

EXAMPLE 4-1

Preparation of optically active 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!-4-hexyl-4-butanolyde (Example Compound No. 19)

(1) Preparation of 4-(2-benzyloxyethyl) phenyl boronic acid

3.8 g (13.0 mmol) of 4-(2-benzyloxyethyl) phenylbromide and 30 ml of dryTHF were cooled to -80° C., and 9.4 ml of n-butyllithium (1.65M) wasdripped to it. Stirring at the foregoing temperature was performed for 3hours, and then mixture solution of 5.68 g (30.2 mmol) oftriisopropoxyboron and 15 ml of dry THF was dripped, and stirring atroom temperature was performed for 13 hours. After the reactions hadbeen completed, 15 ml of 10% hydrochloric acid was added, and extractionwith ethyl acetate was performed. After the extracted solution wasdried, the solvent was removed by filtration. Then, refining wasperformed with a silica gel column chromatography (developing solvent:toluene/ethyl acetate=20/1) so that 3.21 g of 4-(2-benzyloxyethyl)phenyl boronic acid was obtained (yield 64%).

(2) Preparation of 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethylbenzylether

1.27 g (4.96 mmol) of 4-(2-benzyloxyethyl) phenylboronic acid, 1.26 g(4.96 mmol) of 2-chloro-5-decylpyrimidine, 0.19 g of tetrakis(triphenylphosphine) palladium, 8 ml of 2M sodium carbonate, 8 ml oftoluene and 4 ml of ethanol were, under presence of nitrogen, heated at80° C. for 3 hours. After the reactions had been completed, extractionwith toluene was performed and the extracted solution was dried withanhydrous sodium sulfate. The solvent was removed by filtration andrefining was performed by recrystallization (toluene/methanol) so that1.65 g of 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethylbenzylether wasobtained (yield 77%).

(3) Preparation of acetic acid 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl

1.00 g (2.32 mmol) of 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethylbenzylether, 0.036 g (0.116 mmol) of 90% tin bromide, 0.71 g(5.81 mmol) of bromide acetate and 10 ml of dichloromethane were stirredat room temperature for 48 hours. After the reactions had beencompleted, 3M sodium hydrate solution was added to neutralize it. Then,extraction with dichloromethane was performed. The extracted solutionwas dried with anhydrous sodium sulfate and the solvent was removed byfiltration so that 1.49 g of rough acetic acid2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl was obtained.

(4) Preparation of 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethanol

1.49 g of rough acetic acid 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl,0.40 g (10 mmol) of sodium hydrate and 20 ml of ethanol were heated andstirred at 90° C. for one hour. After the reactions had been completed,the solvent was removed by filtration, and 3M hydrochloric acid wasadded so as to be neutralized and extraction with ethyl acetate wasperformed. The extracted solution was dried with anhydrous sodiumsulfate, and then the solvent was removed by filtration. Then, refiningwas performed with a silica gel column chromatography (developingsolvent: toluene/ethyl acetate=20/1) so that 0.65 g of2-{4-(5-decylpyrimidine-2-yl) phenyl}ethanol was obtained (total yieldfrom benzylether derivative 82%).

(5) Preparation of 4-toluene sulfonic acid 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl

0.65 g (1.91 mmol) of 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethanol, 0.36g (1.91 mmol) of 4-toluene sulfonic acid chloride and 1.00 g (12.7 mmol)of pyridine were stirred at room temperature for 4 hours. After thereactions had been completed, cooling was performed, 10 ml of 6Mhydrochloric acid was added, extraction with toluene was performed andthe extracted solution was dried with anhydrous sodium sulfate. Thesolvent was removed by filtration, and then refining was performed witha silica gel column chromatography (developing solvent: toluene) so that0.87 g of 4-toluene sulfonic acid 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl was obtained (yield 92%).

(6) Preparation of 2- 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl!diethylmalonate

0.09 g (2.29 mmol) of 60% sodium hydrate and 0.3 ml of DMF wereinjected, and mixture solution of 0.32 g (2.00 mol) of dimethyl malonateand 1 ml of DMF was dripped to the foregoing materials. Stirring at roomtemperature was performed for 15 minutes, and then mixed solution of0.87 g (1.76 mmol) of 4-toluene sulfonic acid2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl and 2 ml of DMF was dripped,and then heating and stirring at 90° C. were performed for 5 hours.After the reactions had been completed, cooling was performed, water wasadded and extraction with toluene was performed. Then, cleaning withwater and drying were performed. After the solvent was removed byfiltration, refining was performed with a silica gel columnchromatography (developing solvent: toluene/ethyl acetate=20/1! so that0.43 g of 2- 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl!diethyl malonatewas obtained (yield 51%).

(7) Preparation of optically active 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!-4-hexyl-4-butanolyde

0.43 g (0.89 mmol) of 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!diethyl malonate, 0.11 g (0.98 mmol) of t-butoxypotassiumand 4 ml of t-butanol were injected. Then, mixed solution of 0.11 g(0.89 mmol) of optically active 1,2-epoxyoctane and 2 ml of t-butanolwas dripped, and heating and stirring at 90° C. were performed for 3hours. After the reactions had been completed, 6M hydrochloric acid wasadded to make the pH to be 1, and extraction with ethyl acetate wasperformed. The extracted solution was dried, and the solvent was removedby filtration, and then refining was performed with a silica gel columnchromatography (developing solvent: toluene/ethyl acetate=20/1) so that0.03 g of optically active 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!-4-hexyl-4-butanolyde was obtained (yield 7% and meltingpoint 66.3° C.).

EXAMPLE 4-2

Preparation of optically active 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!-4-hexyl-4-butanolyde (Example Compound No. 19) <Fineadjustment of conditions for Example 4-1>

(1) Preparation of 4-(2-benzyloxyethyl) phenyl boronic acid

13.7 g (47.1 mmol) of 4-(2-benzyloxyethyl) phenylbromide and 80 ml ofdry THF were cooled to -75° C., and 34.0 ml of n-butyllithium (1.65M)was dripped to it. Stirring at the foregoing temperature was performedfor 3 hours, and then mixture solution of 12.9 g (68.7 mmol) oftriisopropoxyboron and 50 ml of dry THF was dripped, and stirring at-75° C. was performed for 2 hours and that at room temperature wasperformed for 14 hours. After the reactions had been completed, 50 ml of10% hydrochloric acid was added, and extraction with ethyl acetate wasperformed. After the extracted solution was dried, the solvent wasremoved by filtration. Then, refining was performed with a silica gelcolumn chromatography (developing solvent: toluene/ethyl acetate=20/1)so that 8.62 g of 4-(2-benzyloxyethyl) phenyl boronic acid was obtained(yield 71%).

(2) Preparation of 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethylbenzylether

1.27 g (4.96 mmol) of 4-(2-benzyloxyethyl) phenylboronic acid, 1.26 g(4.96 mmol) of 2-chloro-5-decylpyrimidine, 0.19 g of tetrakis(triphenylphosphine) palladium, 8 ml of 2M sodium carbonate, 8 ml oftoluene and 4 ml of ethanol were, under presence of nitrogen, heated at80° C. for 3 hours. After the reactions had been completed, extractionwith toluene was performed and the extracted solution was dried withanhydrous sodium sulfate. The solvent was removed by filtration andrefining was performed by recrystallization (toluene/methanol) so that1.65 g of 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethylbenzylether wasobtained (yield 77%).

(3) Preparation of acetic acid 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl

1.00 g (2.32 mmol) of 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethylbenzylether, 0.036 g (0.116 mmol) of 90% tin bromide, 0.71 g(5.81 mmol) of bromide acetate and 10 ml of dichloromethane were stirredat room temperature for 48 hours. After the reactions had beencompleted, 3M sodium hydrate solution was added to neutralize it. Then,extraction with dichloromethane was performed. The extracted solutionwas dried with anhydrous sodium sulfate and the solvent was removed byfiltration so that 1.49 g of rough acetic acid2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl was obtained.

(4) Preparation of 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethanol

1.49 g of rough acetic acid 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl,0.40 g (10 mmol) of sodium hydrate and 20 ml of ethanol were heated andstirred at 90° C. for one hour. After the reactions had been completed,the solvent was removed by filtration, and 3M hydrochloric acid wasadded so as to be neutralized and extraction with ethyl acetate wasperformed. The extracted solution was dried with anhydrous sodiumsulfate, and then the solvent was removed by filtration. Then, refiningwas performed with a silica gel column chromatography (developingsolvent: toluene/ethyl acetate=20/1) so that 0.65 g of2-{4-(5-decylpyrimidine-2-yl) phenyl}ethanol was obtained (total yieldfrom benzylether derivative 82%).

(5) Preparation of 4-toluene sulfonic acid 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl

0.65 g (1.91 mmol) of 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethanol, 0.36g (1.91 mmol) of 4-toluene sulfonic acid chloride and 1.00 g (12.7 mmol)of pyridine were stirred at room temperature for 4 hours. After thereactions had been completed, cooling was performed, 10 ml of 6Mhydrochloric acid was added, extraction with toluene was performed andthe extracted solution was dried with anhydrous sodium sulfate. Thesolvent was removed by filtration, and then refining was performed witha silica gel column chromatography (developing solvent: toluene) so that0.87 g of 4-toluene sulfonic acid 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl was obtained (yield 92%).

(6) Preparation of 2- 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl!diethylmalonate

0.30 g (7.52 mmol) of 60% sodium hydrate and 5 ml of DMF were injected,and mixture solution of 1.26 g (7.85 mol) of dimethyl malonate and 2 mlof DMF was dripped to the foregoing materials. Stirring at roomtemperature was performed for 15 minutes, and then mixed solution of3.38 g (6.83 mmol) of 4-toluene sulfonic acid2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl and 10 ml of DMF was dripped,and then heating and stirring at 90° C. were performed for 7 hours.After the reactions had been completed, cooling was performed, water wasadded and extraction with toluene was performed. Then, cleaning withwater and drying were performed. After the solvent was removed byfiltration, refining was performed with a silica gel columnchromatography (developing solvent: toluene/ethyl acetate=20/1! so that2.49 g of 2- 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl!diethyl malonatewas obtained (yield 76%).

(7) Preparation of optically active 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!-4-hexyl-4-butanolyde

1.93 g (4.0 mmol) of 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!diethyl malonate, 0.55 g (4.4 mmol) of t-butoxypotassiumand 15 ml of t-butanol were injected. Then, mixed solution of 0.62 g(4.8 mmol) of optically active (R)-1,2-epoxyoctane and 6 ml of t-butanolwas dripped, and heating and stirring at 90° C. were performed for 6hours. After the reactions had been completed, 6M hydrochloric acid wasadded to make the pH to be 1, and extraction with ethyl acetate wasperformed. The extracted solution was dried, and the solvent was removedby filtration, and then refining was performed with a silica gel columnchromatography (developing solvent: toluene/ethyl acetate=20/1) and byrecrystallization (once with hexane/ethyl acetate and oncehexane/isopropanol) so that 0.69 g of optically active 2-2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl!-4-hexyl-4-butanolyde(mixture ratio of cis/trans=83/17) was obtained (yield 35% and meltingpoint 66.3° C.).

EXAMPLE 5-1

Preparation of optically active 2-(5-hexenyl)-4-hexyl-4-butanolyde(Example Compound No. 513)

(1) Preparation of 2-(5-hexenyl) diethyl malonate

0.59 g (14.7 mmol) of 60% sodium hydrate and 5 ml of DMF were injected,and mixed solution of 2.36 g (14.7 mol) of dimethyl malonate 5 ml of DMFwas dripped. Stirring at room temperature was performed for 15 minutes,and then mixed solution of 2.04 g (12.3 mol) of 6-bromo-1-hexene and 5ml of DMF was dripped. Then, heating and stirring at 90° C. wereperformed for 6 hours. After the reactions had been completed, water wasadded, extraction with ethyl acetate was performed, and cleaning withwater and drying were performed. After the solvent had been removed,distillation under reduced pressure was performed so that 2.78 g of2-(5-hexenyl) diethyl malonate was obtained (yield 93% and melting point100° C. to 110° C./6 torr).

(2) Preparation of optically active 2-(5-hexenyl)-4-hexyl-4-butanolyde

2.30 g (9.5 mmol) of 2-(5-hexenyl) diethyl malonate, 1.30 g (10.4 mmol)of t-butoxypotassium and 20 ml of t-butanol were injected. Then, mixedsolution of 1.22 g (9.5 mmol) of optically active 1,2-epoxyoctane and 6ml of t-butanol was dripped, and heating and stirring at 90° C. wereperformed for 5 hours. After the reactions had been completed, 6Mhydrochloric acid was added to make the pH to be 1, and extraction withethyl acetate was performed. The extracted solution was dried, and thesolvent was removed by filtration, and then refining was performed witha silica gel column chromatography (developing solvent: toluene) so that1.37 g of optically active 2-(5-hexenyl)-4-hexyl-4-butanolyde wasobtained (yield 48%).

EXAMPLE 5-2

Preparation of 2- 6-{4-(5-decylpyrimidine-2-yl)phenyl}hexyl!-4-hexyl-4-butanolyde (Example Compound No. 124)

0.80 g (2.66 mmol) of optically active2-(5-hexenyl)-4-hexyl-4-butanolyde (Example Compound No. 513) and 3 mlof THF were injected, and they were cooled to -17° C. Then, 6.4 ml of9-borabicyclo 3.3.1!nonane (0.5M THF solution) was dripped, and stirringat 0° C. was performed for one hour. Then, stirring at room temperaturewas performed for one hour, and then 0.08 g (0.073 mmol) of tetrakis(triphenylphosphine) palladium, 1.00 g (2.66 mmol) of5-decyl-2-(4-bromophenyl) pyrimidine, 10 ml of DMF, and 0.74 g (5.32mmol) of potassium carbonate were added, and stirring at 60° C. wasperformed for 5 hours. After reactions had been completed, water wasadded, and extraction with ethyl acetate was performed. The extractedsolution was dried, and then the solvent was removed by filtration.Then, refining was performed with a silica gel column chromatography(developing solvent: toluene/ethyl acetate=50/1) and byrecrystallization (hexane/ethyl acetate) so that 0.32 g of 2-6-{4-(5-decylpyrimidine-2-yl) phenyl}hexyl!-4-hexyl-4-butanolyde wasobtained (yield 22% and melting point 64.3° C.).

EXAMPLE 6

Preparation of optically active 2- 2-{4-(2-octylindane-5-yl)phenyl}ethyl!-4-phenyl-4-butanolyde (Example Compound No. 257)

0.70 g (1.40 mmol) of 2- 2-{4-(2-octylindane-5-yl) phenyl}ethyl!diethylmalonate, 0.17 g (1.56 mmol) of t-butoxypotassium and 8 ml of t-butanolwere injected. Then, mixed solution of 0.17 g (1.42 mmol) of opticallyactive styrene oxide and 4 ml of t-butanol was dripped, and heating andstirring at 90° C. were performed for 3 hours. After the reactions hadbeen completed, 6M hydrochloric acid was added to make the pH to be 1,and extraction with ethyl acetate was performed. The extracted solutionwas dried, and the solvent was removed by filtration, and refining wasperformed with a silica gel column chromatography (developing solvent:toluene) and by recrystallization (toluene/methanol) so that 0.08 g ofoptically active 2- 2-{4-(2-octylindane-5-yl)phenyl}ethyl!-4-phenyl-4-butanolyde was obtained (yield 11% and meltingpoint 96.9° C.).

EXAMPLE 7

Preparation of optically active 2- 2-{4-(2-octylindane-5-yl)phenyl}ethyl!-4-(4-methoxyphenyl)-4-butanolyde (Example Compound No.468)

0.70 g (1.40 mmol) of 2- 2-{4-(2-octylindane-5-yl) phenyl}ethyl!diethylmalonate, 0.17 g (1.56 mmol) of t-butoxypotassium and 8 ml of t-butanolwere injected. Then mixed solution of 0.21 g (1.42 mmol) of opticallyactive 4-methoxystyreneoxide and 4 ml of t-butanol was dripped, andheating and stirring at 90° C. were performed for 3 hours. After thereactions had been completed, 6M hydrochloric acid was added to make thepH to be 1, and extraction with ethyl acetate was performed. Theextracted solution was dried, and the solvent was removed by filtration,and refining was performed with a silica gel column chromatography(developing solvent: toluene) and by recrystallization(toluene/methanol) so that 0.05 g of optically active 2-2-{4-(2-octylindane-5-yl) phenyl}ethyl!-4-(4-methoxyphenyl)-4-butanolydewas obtained (yield 7% and melting point 140.7° C.).

EXAMPLE 8

Preparation of optically active 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!-4-phenyl-4-butanolyde (Example Compound No. 229)

0.50 g (1.04 mmol) of 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!diethyl malonate, 0.13 g (1.14 mmol) of t-butoxypotassiumand 3 ml of t-butanol were injected. Then, mixed solution of 0.15 g(1.25 mmol) of optically active styreneoxide and 2 ml of t-butanol wasdripped, and heating and stirring at 90° C. were performed for 3 hours.After the reactions had been completed, 6M hydrochloric acid was addedto make the pH to be 1, and extraction with ethyl acetate was performed.After the extracted solution was dried, and the solvent was removed byfiltration. Then, refining was performed with a silica gel columnchromatography (developing solvent: toluene/ethyl acetate=10/1) and byrecrystallization (methanol) so that 0.09 g of optically active 2-2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl!-4-phenyl-4-butanolyde wasobtained (yield 18% and melting point 79.5° C.).

EXAMPLE 9

Preparation of optically active 2-methyl-4-8-{4-(5-decylpyrimidine-2-yl) phenyl}octyl!-4-butanolyde (ExampleCompound No. 476)

(1) Preparation of optically active1,2-epoxy-8-{4-(5-decylpyrimidine-2-yl) phenyl}decane

1.36 g (8.8 mmol) of optically active 1,2-epoxy-9-decene and 6 ml of THFwere injected, and they were cooled to -17° C. Then, 9-borabicyclo3.3.1!nonane (0.5M THF solution) was dripped, and stirring at 0° C. wasperformed for one hour. Then, stirring at room temperature was performedfor one hour, and then 0.26 g (0.073 mmol) of tetrakis(triphenylphosphine) palladium, 3.00 g (8.00 mmol) of5-decyl-2-(4-bromophenyl) pyrimidine, 10 ml of DMF, and 2.21 g (16.0mmol) of potassium carbonate were added, and stirring at 60° C. wasperformed for 5 hours. After reactions had been completed, water wasadded, and extraction with ethyl acetate was performed. The extractedsolution was dried, and then the solvent was removed by filtration.Then, refining was performed with a silica gel column chromatography(developing solvent: toluene/ethyl acetate=50/1) and byrecrystallization (toluene/methanol) so that 2.10 g of1,2-epoxy-8-{4-(5-decylpyrimidine-2-yl) phenyl}decane was obtained(yield 58%).

(2) Preparation of optically active 2-methyl-4-8-{4-(5-decylpyrimidine-2-yl) phenyl}octyl!-4-butanolyde

0.39 g (2.22 mmol) of 2-methyl diethyl malonate, 0.31 g (2.44 mmol) oft-butoxypotassium and 5 ml of t-butanol were injected. Then, mixedsolution of 1.00 g (2.22 mmol) of optically active compound1,2-epoxy-8-{4-(5-decylpyrimidine-2-yl) phenyl}decane and 6 ml oft-butanol was dripped, and then heating and stirring at 90° C. wereperformed for 4 hours. After the reactions had been completed,6M-hydrochloric acid was added so that the pH was made to be 1, andextraction with ethyl acetate was performed. After the extractedsolution was dried, the solvent was removed by filtration. Then,refining was performed with a silica gel column chromatography(developing solvent: hexane/ethyl acetate=10/1) and by recrystallization(methanol) so that 0.30 g of optically active 2-methyl-4-8-{4-(5-decylpyrimidine-2-yl) phenyl}octyl!-4-butanolyde was obtained(yield 27% and melting point 76.4° C.).

EXAMPLE 10

Preparation of optically active 2- 2-{4-(5-decyloxypyrimidine-2-yl)phenyl}ethyl!-4-hexyl-4-butanolyde (Example Compound No. 483)

(1) Preparation of 2-{4-(5-decyloxypyrimidine-2-yl)phenyl}ethylbenzylether

8.62 g (33.7 mmol) of 4-(2-benzyloxyethyl) phenyl boronic acid, 9.13 g(33.7 mmol) of 2-chloro-5-decyloxypyrimidine, 1.29 g of tetrakis(triphenylphosphine) palladium, 54 ml of 2M-sodium carbonate solution,54 ml of toluene and 27 ml of ethanol were heated at 80° C. for 4 hoursunder presence of nitrogen. After reactions had been completed,extraction with toluene was performed. Then, the extracted solution wasdried with anhydrous sodium sulfate. The solvent was removed byfiltration, and then refining was performed by recrystallization(toluene/methanol) so that 9.30 g of 2-{4-(5-decyloxypyrimidine-2-yl)phenyl}ethylbenzylether was obtained (yield 62%).

(2) Preparation of acetic acid 2-{4-(5-decyloxypyrimidine-2-yl)phenyl}ethyl

9.30 g (20.8 mmol) of 2-{4-(5-decyloxypyrimidine-2-yl)phenyl}ethylbenzylether, 0.279 g (0.116 mmol) of 90% tin bromide, 8.0 g(62.4 mmol) of bromide acetate and 50 ml of dichloromethane were stirredat room temperature for 48 hours. After the reactions had beencompleted, 3M sodium hydrate solution was added to neutralize it, andthen extraction with dichloromethane was performed. The extractedsolution was dried with anhydrous sodium sulfate, and then the solventwas removed by filtration so that 12.5 g of rough acetic acid2-{4-(5-decyloxypyrimidine-2-yl) phenyl}ethyl was obtained.

(3) Preparation of 2-{4-(5-decyloxypyrimidine-2-yl) phenyl}ethanol

12.5 g of rough acetic acid 2-{4-(5-decyloxypyrimidine-2-yl)phenyl}ethyl, 3.78 g (89.7 mmol) of sodium hydrate and 100 ml of ethanolwere heated and stirred at 90° C. for 3 hours. After the reactions hadbeen completed, the solvent was removed by filtration, and 3Mhydrochloric acid was added to neutralize it. Then, extraction withethyl acetate was performed. The extracted solution was dried withanhydrous sodium sulfate, and then the solvent was removed byfiltration. Then, refining was performed with a silica gel columnchromatography (developing solvent: toluene/ethyl acetate=10/1) so that2.0 g of 2-{4-(5-decyloxypyrimidine-2-yl) phenyl}ethanol was obtained(total yield from benzylether derivative 27%).

(4) Preparation of 4-toluene sulfonic acid2-{4-(5-decyloxypyrimidine-2-yl) phenyl}ethyl

2.0 g (5.6 mmol) of 2-{4-(5-decyloxypyrimidine-2-yl) phenyl}ethanol,1.07 g (5.6 mmol) of 4-toluene sulfonic acid chloride and 1.2 g (15.0mmol) of pyridine were stirred at room temperature for 3 hours. Afterthe reactions had been completed, cooling was performed, and 6Mhydrochloric acid was added, and extraction with ethyl acetate wasperformed. Then, the extracted solution was dried with anhydrous sodiumsulfate. After the solvent had been removed by filtration, refining wasperformed with a silica gel column chromatography (developing solvent:toluene) so that 1.68 g of 4-toluene sulfonic acid2-{4-(5-decyloxypyrimidine-2-yl) phenyl}ethyl was obtained (yield 59%).

(5) Preparation of 2- 2-{4-(5-decyloxypyrimidine-2-yl)phenyl}ethyl!diethyl malonate

0.14 g (3.51 mmol) of 60% sodium hydrate and 3 ml of DMF were injected,and mixed solution of 0.59 g (3.67 mol) of dimethyl malonate and 1 ml ofDMF was dripped. Stirring at room temperature was performed for 15minutes, and mixed solution of 1.63 g (3.19 mmol) of 4-toluene sulfonicacid 2-{4-(5-decyloxypyrimidine-2-yl) phenyl}ethyl and 5 ml of DMF wasdripped. Then, heating and stirring at 90° C. was performed for 7 hours.After the reactions had been completed, cooling was performed, water wasadded, extraction with toluene was performed, cleaning with water anddrying were performed. After the solvent had been removed by filtration,refining was performed with a silica gel column chromatography(developing solvent: hexane/ethyl acetate=5/1) so that 0.98 g of -2-{4-(5-decyloxypyrimidine-2-yl) phenyl}ethyl!diethyl malonate wasobtained (yield 62%)

(6) Preparation of optically active 2- 2-{4-(5-decyloxypyrimidine-2-yl)phenyl}ethyl!-4-hexyl-4-butanolyde

0.4 g (0.8 mmol) of 2- 2-{4-(5-decyloxypyrimidine-2-yl)phenyl}ethyl!diethyl malonate, 0.11 g (0.88 mmol) of t-butoxypotassiumand 3 ml of t-butanol were injected. Then, mixed solution of 0.12 g(0.97 mmol) of optically active (R)-1,2-epoxyoctane and 1 ml oft-butanol was dripped. Then, heating and stirring at 90° C. wereperformed for 6 hours. After the reactions had been completed, 6Mhydrochloric acid was added to make the pH to be 1, and then extractionwith ethyl acetate was performed. The extracted solution was dried, andthe solvent was removed by filtration. Then, refining was performed witha silica gel column chromatography (developing solvent: hexane/ethylacetate=5/1) and by recrystallization (hexane/ethyl acetate) so that 0.1g of optically active 2- 2-{4-(5-decyloxypyrimidine-2-yl)phenyl}ethyl!-4-hexyl-4-butanolyde (mixture ratio of cis/trans=75/25)was obtained (yield 25% and melting point 73.3° C.).

EXAMPLE 11

Preparation of optically active 2- 6-{4-(5-decyloxypyrimidine-2-yl)phenyl}hexyl!-4-hexyloxymethyl butanolyde (Example Compound No. 501)

0.54 g (1.08 mmol) of 2- 2-{4-(5-decyloxypyrimidine-2-yl)phenyl}ethyl!diethyl malonate, 0.15 g (1.19 mmol) of t-butoxypotassiumand 3 ml of t-butanol were injected. Then, mixed solution of 0.21 g(1.30 mmol) of optically active (R)-hexylglycidyl ether and 1 ml oft-butanol was dripped, and then heating and stirring at 90° C. wereperformed for 4 hours. After the reactions had been completed, 6Mhydrochloric acid was added to make pH to be 1, and extraction withethyl acetate was performed. After the extracted solution had beendried, the solvent was removed by filtration. Then, refining wasperformed with a silica gel column chromatography (developing solvent:hexane/ethyl acetate=5/1) so that 0.10 g of optically active trans-2-6-{4-(5-decyloxypyrimidine-2-yl) phenyl}hexyl!-4-hexyloxymethylbutanolyde and 0.08 g of optically active cis-2-6-{4-(5-decyloxypyrimidine-2-yl) phenyl}hexyl!-4-hexyloxymethylbutanolyde were obtained (melting point of the trans structure 31.1° C.and that of the cis structure 53.3° C.).

EXAMPLE 12

Preparation of optically active 2-(3-butenyl)-4-hexyl-4-butanolyde(Example Compound No. 511)

(1) Preparation of 2-(3-butenyl) diethyl malonate

20 g (870 mmol) of metal sodium and 340 ml of ethanol were injected, andthen 112 g (700 mmol) of dimethyl malonate was added. Stirring at roomtemperature was performed for 15 minutes, and then 97 g (719 mmol) of4-bromo-1-butene was added. Then, heating and stirring at 90° C. wereperformed for 15 hours. After the reactions had been completed, ethanolwas removed by filtration, and then 500 ml of water was added. Then,extraction with ether was performed, and cleaning with water and dryingwere performed. After the solvent had been removed by filtration,distillation was performed under reduced pressure so that 112 g of2-(3-butenyl) diethyl malonate was obtained (yield 58% and melting point90° C. to 100° C./4 torr).

(2) Preparation of optically active 2-(3-butenyl)-4-hexyl-4-butanolyde

67 g (313 mmol) of 2-(3-butenyl) diethyl malonate, 38.6 g (344 mmol) oft-butoxypotassium and 300 ml of t-butanol were injected. Then, 40 g (313mmol) of optically active (R)-1,2-epoxyoctane was dripped, and thenheating and stirring at 90° C. were performed for 20 hours. After thereactions had been completed, 6M hydrochloric acid was added to make thepH to be 1. Then, extraction with ethyl acetate was performed, and theextracted solution was dried. Then, the solvent was removed byfiltration and refining was performed by distillation under reducedpressure and by a silica gel column chromatography (developing solvent:hexane/ethyl acetate=16/1) so that 21.6 g of optically active2-(3-butenyl)-4-hexyl-4-butanolyde was obtained (yield 31% and meltingpoint 95° C. to 105° C./1 torr).

EXAMPLE 13

Preparation of 2- 4-{4-(5-decylpyrimidine-2-yl)phenyl}butyl!-4-hexyl-4-butanolyde (Example Compound No. 504)

0.72 g (2.66 mmol) of optically active2-(3-butenyl)-4-hexyl-4-butanolyde and 3 ml of THF were injected, andthey were cooled to -17° C. Then, 6.4 ml of 9-borabicyclo 3.3.1!nonane(0.5M THF solution) was dripped, and stirring at 0° C. was performed forone hour. Furthermore, stirring at room temperature was performed forone hour, and then 0.08 g (0.073 mmol) of tetrakis (triphenylphosphine)palladium, 1.00 g (2.66 mmol) of 5-decyl-2-(4-bromophenyl) pyrimidine,10 ml of DMF and 0.74 g (5.32 mmol) of potassium carbonate were added.Then, they were stirred at 60° C. for 5 hours. After the reactions hadbeen completed, water was added, and extraction with ethyl acetate wasperformed. After the extracted solution had been dried, the solvent wasremoved by filtration. Then, refining was performed with a silica gelcolumn chromatography (developing solvent: hexane/ethyl acetate=50/1)and by recrystallization (once by hexane/ethyl acetate and once byacetone) so that 0.10 g of optically active 2-4-{4-(5-decylpyrimidine-2-yl) phenyl}butyl!-4-hexyl-4-butanolyde(mixture ratio of cis/trans=97/3) was obtained (yield 7% and meltingpoint 57.2° C.).

EXAMPLE 14

Preparation of optically active 2-(2-propenyl)-4-hexyl-4-butanolyde(Example Compound No. 510)

(1) Preparation of 2-(2-propenyl) diethyl malonate

19 g (826 mmol) of metal sodium and 420 ml of ethanol were injected, andthen 135 g (844 mmol) of dimethyl malonate was added. Stirring at roomtemperature was performed for 15 minutes, and then 100 g (826 mmol) ofallylbromide was added. Then, heating and stirring at 90° C. wereperformed for 15 hours. After the reactions had been completed, ethanolwas removed by filtration, and then 500 ml of water was added. Then,extraction with ether was performed, and cleaning with water and dryingwere performed. After the solvent had been removed by filtration,refining was performed with a silica gel column chromatography(developing solvent: hexane/ethyl acetate 4/1) so that 89 g of2-(2-propenyl) diethyl malonate was obtained (yield 54%).

(2) Preparation of 2-(2-propenyl)-4-hexyl-4-butanolyde

73 g (365 mmol) of 2-(2-propenyl) diethyl malonate, 44 g (392 mmol) oft-butoxypotassium and 400 ml of t-butanol were injected. Then, 47.4 g(313 mmol) of optically active (R)-1,2-epoxyoctane was dripped, and thenheating and stirring at 90° C. were performed for 20 hours. After thereactions had been completed, 6M hydrochloric acid was added to make thepH to be 1. Then, extraction with ethyl acetate was performed, and theextracted solution was dried. Then, the solvent was removed byfiltration and refining was performed by distillation under reducedpressure and by a silica gel column chromatography (developing solvent:hexane/ethyl acetate=20/1) so that 2.9 g of optically activetrans-2-(2-propenyl)-4-hexyl-4-butanolyde and 17.1 g of optically activecis-2-(2-propenyl)-4-hexyl-4-butanolyde were obtained (yield 26% andmelting point 80° C. to 90° C./1 torr).

EXAMPLE 15

Preparation of optically active trans-2- 3-{4-(5-decylpyrimidine-2-yl)phenyl}propyl!-4-hexyl-4-butanolyde (Example Compound No. 505)

0.69 g (2.66 mmol) optically activetrans-2-(2-propenyl)-4-hexyl-4-butanolyde and 3 ml of THF were injected,and they were cooled to -17° C. Then, 6.4 ml of 9-borabicyclo3.3.1!nonane (0.5M THF solution) was dripped, and stirring at 0° C. wasperformed for one hour. Then, stirring at room temperature was performedfor one hour, and then 0.08 g (0.073 mmol) of tetrakis(triphenylphosphine) palladium, 1.18 g (2.66 mmol) oftrifuoromethanesulfonic acid 4-(5-decylpyrimidine-2-yl) phenyl, 10 ml ofDMF, and 0.74 g (5.32 mmol) of potassium carbonate were added, andstirring at 60° C. was performed for 5 hours. After reactions had beencompleted, water was added, and extraction with ethyl acetate wasperformed. The extracted solution was dried, and then the solvent wasremoved by filtration. Then, refining was performed with a silica gelcolumn chromatography (developing solvent: hexane/ethyl acetate=20/1)and by recrystallization (acetone) so that 0.16 g of optically activetrans-2- 3-{4-(5-decylpyrimidine-2-yl)phenyl}propyl!-4-hexyl-4-butanolyde was obtained (yield 12% and meltingpoint 57.9° C.).

EXAMPLE 16

Preparation of optically active cis-2- 3-{4-(5-decylpyrimidine-2-yl)phenyl}propyl!-4-hexyl-4-butanolyde (Example Compound No. 505)

0.69 g (2.66 mmol) optically activecis-2-(2-propenyl)-4-hexyl-4-butanolyde and 3 ml of THF were injected,and they were cooled to -17° C. Then, 6.4 ml of 9-borabicyclo3.3.1!nonane (0.5M THF solution) was dripped, and stirring at 0° C. wasperformed for one hour. Then, stirring at room temperature was performedfor one hour, and then 0.08 g (0.073 mmol) of tetrakis(triphenylphosphine) palladium, 1.18 g (2.66 mmol) oftrifuoromethanesulfonic acid 4-(5-decylpyrimidine-2-yl) phenyl, 10 ml ofDMF, and 0.74 g (5.32 mmol) of potassium carbonate were added, andstirring at 60° C. was performed for 5 hours. After reactions had beencompleted, water was added, and extraction with ethyl acetate wasperformed. The extracted solution was dried, and then the solvent wasremoved by filtration. Then, refining was performed with a silica gelcolumn chromatography (developing solvent: hexane/ethyl acetate=20/1)and by recrystallization (acetone) so that 0.30 g of optically activecis-2- 3-{4-(5-decylpyrimidine-2-yl) phenyl}propyl!-4-hexyl-4-butanolydewas obtained (yield 22% and melting point 73.0° C.).

EXAMPLE 17

Preparation of optically active 2- 3-{2-(4-decylphenyl) pyrimidine-5-yl)phenyl}butyl!-4-hexyl-4-butanolyde (Example Compound No. 175)

1.09 g (3.99 mmol) of optically active2-(3-butenyl)-4-hexyl-4-butanolyde and 3 ml of THF were injected, andthey were cooled to -17° C. Then, 9.6 ml of 9-borabicyclo 3.3.1!nonane(0.5M THF solution) was dripped, and stirring at 0° C. was performed forone hour. Then, stirring at room temperature was performed for one hour,and then 0.13 g (0.073 mmol) of tetrakis (triphenylphosphine) palladium,1.77 g (3.99 mmol) of trifuoromethanesulfonic acid2-(4-decyphenyl)pyrimidine-5-yl, 10 ml of DMF, and 1.11 g (7.98 mmol) ofpotassium carbonate were added, and stirring at 60° C. was performed for5 hours. After reactions had been completed, water was added, andextraction with ethyl acetate was performed. The extracted solution wasdried, and then the solvent was removed by filtration. Then, refiningwas performed with a silica gel column chromatography (developingsolvent: hexane/ethyl acetate=5/1) and by recrystallization (acetone) sothat 0.42 g of optically active 2- 3-{2-(4-decylphenyl) pyrimidine-5-yl)phenyl}butyl!-4-hexyl-4-butanolyde was obtained (yield 20% and meltingpoint 84.8° C.).

EXAMPLE 18

Preparation of 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!-4-butyl-4-butanolyde (Example Compound No. 11)

0.43 g (0.89 mmol) of 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!diethyl malonate, 0.11 g (0.98 mmol) of t-butoxypotassiumand 4 ml of t-butanol were injected. Then, mixed solution of 0.11 g(1.07 mmol) of optically active (R)-1,2-epoxyhexane and 2 ml oft-butanol was dripped, and heating and stirring at 90° C. were performedfor 6 hours. After the reactions had been completed, 6M hydrochloricacid was added to make pH to be 1, and extraction with ethyl acetate wasperformed. After the extracted solution had been dried, the solvent wasremoved by filtration. Then, refining was performed with a silica gelcolumn chromatography (developing solvent: hexane/ethyl acetate 10/1)and by recrystallization (acetone) so that 0.05 g of 2-2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl!-4-butyl-4-butanolyde wasobtained (yield 12% and melting point 62° C.).

EXAMPLE 19

Preparation of 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!-4-propyl-4-butanolyde (Example Compound No. 503)

0.92 g (1.91 mmol) of 2- 2-{4-(5-decylpyrimidine-2-yl)phenyl}ethyl!diethyl malonate, 0.26 g (2.10 mmol) of t-butoxypotassiumand 5 ml of t-butanol were injected. Then, mixed solution of 0.22 g(2.29 mmol) of optically active (R)-1,2-epoxypentane and 2 ml oft-butanol was dripped, and heating and stirring at 90° C. were performedfor 6 hours. After the reactions had been completed, 6M hydrochloricacid was added to make pH to be 1, and extraction with ethyl acetate wasperformed. After the extracted solution had been dried, the solvent wasremoved by filtration. Then, refining was performed with a silica gelcolumn chromatography (developing solvent: hexane/ethyl acetate 10/1)and by recrystallization (acetone) so that 0.22 g of 2-2-{4-(5-decylpyrimidine-2-yl) phenyl}ethyl!-4-propyl-4-butanolyde wasobtained (yield 26% and melting point 54° C.).

EXAMPLE 20

Preparation of 2- 4-{4-(4-hexyl-4-butanolyde-2-yl)butyl}phenyl!-5-{4-(4-hexyl-4-butanolyde-2-yl) butyl}pyrimidine (ExampleCompound No. 502)

2.0 g (7.34 mmol) of optically active 2-(3-butenyl)-4-hexyl-4-butanlydeand 9 ml of THF were injected, and they were cooled to -17° C. Then,17.7 ml of 9-borabicyclo 3.3.1!nonane (0.5M THF solution) was dripped,and stirring at 0° C. was performed for one hour. Furthermore, stirringat room temperature was performed for one hour, and then 0.16 g (0.073mmol) of tetrakis (triphenylphosphine) palladium, 0.94 g (2.45 mmol) oftrifluoromethane sulfonic acid 2-(4-bromophenyl) pyrimidine-5-yl, 10 mlof DMF and 1.35 g (9.8 mmol) of potassium carbonate were added. Then,they were stirred at 60° C. for 5 hours. After the reactions had beencompleted, water was added, and extraction with ethyl acetate wasperformed. After the extracted solution had been dried, the solvent wasremoved by filtration. Then, refining was performed with a silica gelcolumn chromatography (developing solvent: hexane/ethyl acetate=5/1) andby recrystallization (once by hexane/ethyl acetate and once bytoluene/methanol) so that 0.20 g of 2- 4-{4-(4-hexyl-4-butanolyde-2-yl)butyl}phenyl!-5-{4-(4-hexyl-4-butanolyde-2-yl) butyl}pyrimidine wasobtained (yield 13%).

Phase Transition Temperature (°C.) ##STR13## where S3 is undefinedsmectic phase

EXAMPLE 21

Preparation of optically active 2-vinyl-4-hexyl-4-butanolyde (ExampleCompound No. 509)

12.8 g (100 mmol) of naphthalene and 100 ml of dry THF were injected,and 1.4 g (200 mmol) of lithium was added at room temperature. Stirringwas performed for 30 minutes, and then 14.6 g (200 mmol) of diethylaminewas added at room temperature and they were stirred for 30 minutes.Then, mixed solution of 8.6 g (100 mmol) of vinyl acetate and 50 ml ofdry THF was dripped at a temperature of -10° C. or lower. Stirring wasperformed at the foregoing temperature for 30 minutes, and then 12.8 g(100 mol) of (R)-1,2-epoxyoctane was dripped at a temperature of -10° C.or lower. Then, stirring at the foregoing temperature was performed for30 minutes, and heat reflux was performed for 2 hours. After thereactions had been completed, cooling was performed, and they wereimmersed into ice water, and hydrochloric acid was added to be madeacid. Extraction with diisopropyl ether was performed, and cleaning withwater was performed. Then, anhydrous magnesium sulfate was added to bedried. After the solvent had been removed by filtration, 18.8 g ofobtained carboxylic acid was added to 20 ml of diisopropyl ether. Then,stirring was performed at 40° C. for 9 hours. After the reactions hadbeen completed, the solvent was removed by filtration. Then, refiningwas performed with a silica gel column chromatography (developingsolvent: hexane/ethyl acetate=10/1) so that 2.75 g of optically active2-vinyl-4-hexyl-4-butanolyde was obtained (yield 14%).

EXAMPLE 22

Preparation of optically active 4-(3-butenyl)-2-hexyl-4-butanolyde(Example Compound No. 522)

54.8 g (225 mmol) of 2-hexyl diethyl malonate, 25.2 g (225 mmol) oft-butoxypotassium and 500 ml of t-butanol were injected. Then, 20 g (204mmol) of optically active (R)-1,2-epoxy-5-hexene was dripped, andheating and stirring at 90° C. were performed for 7 hours. After thereactions had been completed, 6M hydrochloric acid was added to make thepH to be 1, and extraction with ethyl acetate was performed. After theextracted solution had been dried, the solvent was removed byfiltration. Then, refining was performed by distillation under reducedpressure and with a silica gel column chromatography (developingsolvent: hexane/ethyl acetate 10/1) so that 24 g of optically active4-(3-butenyl)-2-hexyl-4-butanolyde was obtained (yield 53%).

EXAMPLE 23

Preparation of optically active 4- 4-{4-(5-decylpyrimidine-2-yl)phenyl}butyl!-2-hexyl-4-butanolyde (Example Compound No. 506)

0.84 g (3.74 mmol) of 4-(3-butenyl)-2-hexyl-4-butanolyde and 2 ml of THFwere injected, and they were cooled to -17° C. Then, 8.0 ml of9-borabicyclo 3.3.1!nonane (0.5M THF solution) was dripped, and stirringwas performed at 0° C. for one hour. Then, stirring was performed atroom temperature for one hour, and 0.04 g of tetrakis(triphenylphosphine) palladium, 0.50 g (1.33 mmol) of5-decyl-2-(4-bromophenyl) pyrimidine, 6 ml of DMF and 0.37 g ofpotassium carbonate were added, and they were stirred at 60° C. for 7hours. After the reactions had been completed, water was added, andextraction with ethyl acetate was performed. After the extractedsolution had been dried, the solvent was removed by filtration. Then,refining was performed with a silica gel column chromatography(developing solvent: hexane/ethyl acetate=5/1) and by recrystallizationso that 0.20 g of optically active 4- 4-{4-(5-decylpyrimidine-2-yl)phenyl}butyl!-2-hexyl-4-butanolyde was obtained.

EXAMPLE 24

Preparation of optically active 4- 4-{4-(4-pentylcyclohexyl)phenyl}butyl!-2-hexyl-4-butanolyde (Example Compound No. 507)

0.84 g (3.74 mmol) of optically active4-(3-butenyl)-2-hexyl-4-butanolyde and 2 ml of THF were injected, andthey were cooled to -17° C. Then, 8 ml of 9-borabicyclo 3.3.1!nonane(0.5M THF solution) was dripped, and stirring was performed at 0° C. forone hour. Then, stirring at room temperature was performed for one hour,and then 0.04 g of tetrakis (triphenylphosphine) palladium, 0.42 g (1.36mmol) of 4-(4-pentylcyclohexyl) phenylbromide, 6 ml of DMF and 0.37 g ofpotassium carbonate were added, and they were stirred at 60° C. for 7hours. After the reactions had been completed, water was added andextraction with ethyl acetate was performed. After the extractedsolution had been dried, the solvent was removed by filtration. Then,refining was performed with a silica gel column chromatography(developing solvent: hexane/ethyl acetate=5/1) and by recrystallizationso that 0.20 g of optically active 4- 4-{4-(4-pentylcyclohexyl)phenyl}butyl!-2-hexyl-4-butanolyde was obtained (melting point 83.9°C.).

EXAMPLE 25

The following compounds containing Example Compound No. 5 prepared inExample 2 were mixed with the following parts by weight so that liquidcrystal composition A was prepared.

    ______________________________________                                        C.sub.6 H.sub.13 -Py2-Ph-OC.sub.12 H.sub.25                                                            4.2                                                  C.sub.8 H.sub.17 -Py2-Ph-OC.sub.9 H.sub.19                                                             8.4                                                  C.sub.8 H.sub.17 -Py2-Ph-OC.sub.10 H.sub.21                                                            8.4                                                  C.sub.9 H.sub.19 -Py2-Ph-OC.sub.6 H.sub.17                                                             4.2                                                  C.sub.10 H.sub.21 O-Ph-COO-Ph-OCH.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                    27.5                                                 C.sub.6 H.sub.13 -Btb2-Ph-OC.sub.8 H.sub.17                                                            21.1                                                 C.sub.5 H.sub.11 -Ph-Td-Ph-C.sub.5 H.sub.11                                                            5.3                                                  C.sub.6 H.sub.13 -Ph-Td-Ph-C.sub.4 H.sub.9                                                             5.3                                                  C.sub.11 H.sub.23 -Py2-Ph-OCO-Tn-C.sub.4 H.sub.9                                                       5.3                                                  C.sub.11 H.sub.23 -Py2-Ph3F-OCO-Tn-C.sub.4 H.sub.9                                                     5.3                                                  C.sub.6 H.sub.13 *CHF(CH.sub.2).sub.2 O-Ph-Ph-(CH.sub.2).sub.2 -L1-C.sub.6     H.sub.13                5.0                                                  ______________________________________                                    

The phase transition temperature of the liquid crystal composition A isas follows: ##STR14##

EXAMPLE 26

Two glass plates each having a thickness of 0.7 mm were prepared, and anITO film was formed on the glass plate so that an electrode, to whichvoltage was applied, was formed. Then, SiO₂ was evaporated on the ITOfilm so that an insulating layer was formed. Then, isopropyl alcoholsolution containing silane coupling material (KBM-602 manufactured byShinetsu Kagaku) by 0.2% was applied for 15 seconds by a spinnerrotating at a rotational speed of 2000 rpm so that surface treatment wasperformed. Then, heating and drying were performed at 120° C. for 20minutes. Furthermore, the glass plates with the ITO films, furthersubjected to surface treatment, were, for 15 seconds, applied withdimethyl acetoamide solution containing polyimide resin precursor(SP-510 manufactured by Toray) by 1.5% by a spinner rotating at arotational speed of 2000 rpm. After a desired film had been formed, heatshrinkage baking process was performed at 300° C. for 60 minutes. Thus,a film having a thickness of about 250 Å was applied.

The baked film was subjected to a rubbing process using acetate filling,and then it was cleaned with isopropyl alcohol solution. Then, silicabeads having an average diameter of 2 μm were placed on one of the glassplates in such a manner that the axes of the rubbing processes runparallel to one another. Then, an adhesive sealant ("LiqussoBond"manufactured by Chisso) was used to bond the glass plates to each other.Then, the glass plates were heated to 100° C. for 60 minutes so that acell was manufactured. Then, the liquid crystal composition B mixed inExample 10 was, in an isotropic fluid state, injected into the cell.Then, the cell was gradually cooled from the anisotropic phase to 25° C.at a rate of 20° C./hour so that a liquid crystal device (ferroelectricliquid crystal device) was manufactured. The thickness of the cell wasmeasured by a Berek phase plate, resulting in about 2 μm. Thethus-manufactured liquid crystal device was used to measure theintensity of the spontaneous polarization. The results are as follows:

    ______________________________________                                                   10° C.                                                                           30° C.                                                                          40° C.                                   ______________________________________                                        Spontaneous Polarization                                                                   11.6 nc/cm.sup.2                                                                          8.7 nc/cm.sup.2                                                                        5.8 nc/cm.sup.2                             ______________________________________                                    

EXAMPLE 27

In the composition according to Example 25, Example Compound No. 47manufactured in Example 3 was used in place of the Example Compound No.5 so that liquid crystal composition B was prepared. The phasetransition temperature of the liquid crystal composition B was asfollows: ##STR15##

A ferroelectric liquid crystal liquid crystal device was manufactured bythe same method as that of Example 26 except liquid crystal compositionB being injected into the cell so that the spontaneous polarization wasmeasured. The results are were as follows:

    ______________________________________                                                   10° C.                                                                           30° C.                                                                          40° C.                                   ______________________________________                                        Spontaneous Polarization                                                                   7.8 nc/cm.sup.2                                                                           5.5 nc/cm.sup.2                                                                        4.5 nc/cm.sup.2                             ______________________________________                                    

EXAMPLE 28

Example Compound No. 19 manufactured in Example 4 was used in place ofthe Example Compound No. 5 according to Example 25 so that liquidcrystal composition C was prepared. The phase transition temperature ofthe liquid crystal composition C was as follows: ##STR16##

A ferroelectric liquid crystal liquid crystal device was manufactured bythe same method as that of Example 11 except liquid crystal compositionC being injected into the cell so that the spontaneous polarization wasmeasured. The results are were as follows:

    ______________________________________                                                   10° C.                                                                           30° C.                                                                           40° C.                                  ______________________________________                                        Spontaneous Polarization                                                                   15.2 nc/cm.sup.2                                                                          12.2 nc/cm.sup.2                                                                        10.1 nc/cm.sup.2                           ______________________________________                                    

EXAMPLE 29

Example Compound No. 257 manufactured in Example 6 was used in place ofthe Example Compound No. 5 according to Example 25 so that liquidcrystal composition D was prepared. The phase transition temperature ofthe liquid crystal composition D was as follows: ##STR17##

A ferroelectric liquid crystal liquid crystal device was manufactured bythe same method as that of Example 11 except liquid crystal compositionD being injected into the cell so that the spontaneous polarization wasmeasured. The results are were as follows:

    ______________________________________                                                   10° C.                                                                           30° C.                                                                           40° C.                                  ______________________________________                                        Spontaneous Polarization                                                                   9.0 nc/cm.sup.2                                                                           7.1 nc/cm.sup.2                                                                         5.0 nc/cm.sup.2                            ______________________________________                                    

EXAMPLE 30

Example Compound No. 229 manufactured in Example 8 was used in place ofthe Example Compound No. 5 according to Example 25 so that liquidcrystal composition E was prepared. The phase transition temperature ofthe liquid crystal composition E was as follows: ##STR18##

A ferroelectric liquid crystal liquid crystal device was manufactured bythe same method as that of Example 11 except liquid crystal compositionE being injected into the cell so that the spontaneous polarization wasmeasured. The results are were as follows:

    ______________________________________                                                   10° C.                                                                           30° C.                                                                           40° C.                                  ______________________________________                                        Spontaneous Polarization                                                                   14.5 nc/cm.sup.2                                                                          11.5 nc/cm.sup.2                                                                        9.1 nc/cm.sup.2                            ______________________________________                                    

As can be understood from Examples 25 to 30, addition of the opticallyactive compound according to the present invention to another liquidcrystal compound in a small quantity will enable a liquid crystalcomposition having a large spontaneous polarization to be manufactured.Thus, it can be understood that the optically active compound accordingto the present invention has great performance for attaining thespontaneous polarization.

EXAMPLE 31

The following compounds were mixed with the following parts by weight sothat liquid crystal composition F was prepared.

    ______________________________________                                        Constitutional Formula Parts by Weight                                        ______________________________________                                        C.sub.9 H.sub.19 -Py2-Ph-OC.sub.9 H.sub.19                                                           6                                                      C.sub.10 H.sub.21 -Py2-Ph-OC.sub.8 H.sub.17                                                          6                                                      C.sub.8 H.sub.17 O-Pr1-Ph-O(CH.sub.2).sub.5 *CH(CH.sub.3)C.sub.2 H.sub.5                             7                                                      C.sub.11 H.sub.23 O-Py2-Ph-O(CH.sub.2).sub.2 *CH(CH.sub.3)C.sub.2                                    14 ub.5                                                C.sub.10 H.sub.21 -Pr2-Ph-C.sub.6 H.sub.13                                                           8                                                      C.sub.6 H.sub.13 -Py2-Ph-Ph-C.sub.4 H.sub.9                                                          4                                                      C.sub.8 H.sub.17 -Ph-Pr2-Ph-OC.sub.5 H.sub.11                                                        2                                                      C.sub.3 H.sub.7 -Cy-COO-Ph-Py1-C.sub.12 H.sub.25                                                     10                                                     C.sub.5 H.sub.11 -Cy-COO-Ph-Py1-C.sub.12 H.sub.25                                                    5                                                      C.sub.10 H.sub.21 O-Ph-COS-Ph-OC.sub.8 H.sub.17                                                      10                                                     C.sub.6 H.sub.13 -Ph-COO-Ph-Ph-OCH.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                 7                                                      C.sub.3 H.sub.7 -Cy-CH.sub.2 O-Ph-Py1-C.sub.8 H.sub.17                                               7                                                      C.sub.10 H.sub.21 -Ph-Ph-OCH.sub.2 -Ph-C.sub.7 H.sub.15                                              5                                                      C.sub.12 H.sub.25 -Py2-Ph-OCH.sub.2 *CH(F)C.sub.5 H.sub.11                                           2                                                      C.sub.5 H.sub.11 -Cy-COO-Ph-OCH.sub.2 *CH(F)C.sub.6 H.sub.13                                         2                                                      C.sub.12 H.sub.25 O-Ph-Pa-COO(CH.sub.2).sub.3 *CH(CH.sub.3)C.sub.2            H.sub.5                2                                                      C.sub.12 H.sub.25 O-Ph-Pa-O(CH.sub.2).sub.3 *CH(CH.sub.3)OC.sub.3                                    3.sub.7                                                ______________________________________                                    

Furthermore, the following example compounds were mixed to the liquidcrystal composition F with the following parts by weight so that liquidcrystal composition G was prepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.      Constitutional Formula                                                                           Parts by Weight                                   ______________________________________                                        15       C.sub.13 H.sub.27 -Py2-Ph-(CH.sub.2).sub.2 -L1-C.sub.5 H.sub.11                                  2                                                 51       C.sub.12 H.sub.25 -Btb2-Ph-(CH.sub.2).sub.2 -L1-C.sub.6 H.sub.13                                 1                                                 83       C.sub.4 H.sub.9 -Ph-Tn-(CH.sub.2).sub.2 -L1-C.sub.7 H.sub.15                                     2                                                          F                  95                                                ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 11 except liquid crystal composition G being injected into thecell. A peak-to-peak voltage Vpp=20 V was applied to detect opticalresponse (change in the transmitted light quantity 0 to 90%) undercrossed-Nicol so that the response speed (hereinafter called "opticalresponse speed") was measured. The results were as follows:

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            391 μsec 209 μsec                                                                            113 μsec                                  ______________________________________                                    

Comparative Example 1

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition F being injected into thecell. The optical response speed was measured by the same method as thatof Example 16. The results were as follows:

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            668 μsec 340 μsec                                                                            182 μsec                                  ______________________________________                                    

EXAMPLE 32

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 31 so that liquid crystal composition H wasprepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                        22      C.sub.7 H.sub.15 OCO-Cy-Ph-(CH.sub.2).sub.2 L1-C.sub.14 H.sub.29                                   1                                                41      C.sub.6 H.sub.13 -Gp1-Ph-(CH.sub.2).sub.2 -L1-C.sub.12 H.sub.25                                    2                                                100     C.sub.3 H.sub.7 -Ph-Ph-Pyl-(CH.sub.2).sub.2 -L1-C.sub.7 H.sub.15                                   2                                                        F                    95                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition H being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            413 μsec 220 μsec                                                                            121 μsec                                  ______________________________________                                    

EXAMPLE 33

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 31 so that liquid crystal composition I wasprepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                         9      C.sub.8 H.sub.17 O-Ph-COO-Ph-(CH.sub.2).sub.2 -L1-C.sub.6                     H.sub.13             1                                                60      C.sub.6 H.sub.13-Ph-Pr2-Ph-(CH.sub.2).sub.2-L1-C.sub.6 H.sub.13                                    2                                                84      C.sub.8 H.sub.17 -Ph-Tz1-(CH.sub.2).sub.2 -L1-C.sub.12 H.sub.25                                    2                                                        F                    95                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition H being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            435 μsec 230 μsec                                                                            127 μsec                                  ______________________________________                                    

EXAMPLE 34

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 31 so that liquid crystal composition J wasprepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                            Parts by Weight                                   ______________________________________                                        115     C.sub.8 H.sub.17 -Prl-Ph-(CH.sub.2)5-L1-C.sub.8 H.sub.17                                          2                                                 134     C.sub.5 H.sub.11 -Tz1-Ph-(CH.sub.2).sub.8 -L1-C.sub.8 H.sub.17                                    2                                                 160     C.sub.6 H.sub.13 -Ph-Ph-Ph-(CH.sub.2).sub.6 -L1-C.sub.3 H.sub.7                                   2                                                         F                   95                                                ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition J being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            451 μsec 244 μsec                                                                            135 μsec                                  ______________________________________                                    

EXAMPLE 35

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 31 so that liquid crystal composition K wasprepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                        236     C.sub.10 H.sub.21 -Pd-Ph-(CH.sub.2).sub.2 -L1-Ph-OCH.sub.3                                         1                                                256     C.sub.11 H.sub.23 -Id1-Ph-(CH.sub.2).sub.4 -L2-Ph-H                                                2                                                299     C.sub.11 H.sub.23 -Ph-Np-(CH.sub.2).sub.2 -L1-Ph-C.sub.6 H.sub.13                                  2                                                        F                    95                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition K being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            430 μsec 231 μsec                                                                            128 μsec                                  ______________________________________                                    

EXAMPLE 36

The following example compounds were mixed with the following parts byweight so that liquid crystal composition L was prepared.

    ______________________________________                                                                    Parts by                                          Constitutional Formula      Weight                                            ______________________________________                                        C.sub.7 H.sub.15 -Py2-Ph-OC.sub.9 H.sub.19                                                                12                                                C.sub.11 H.sub.23 -Py2-Ph-OC.sub.6 H.sub.13                                                               10                                                C.sub.8 H.sub.17 -Pr2-Ph-O(CH.sub.2).sub.5 *CH(CH.sub.3)C.sub.2 H.sub.5                                   10                                                C.sub.10 H.sub.21 -Py2-Ph-O(CH.sub.2).sub.4 CH(CH.sub.3)OCH.sub.3                                         3                                                 C.sub.8 H.sub.17 -Py2-Ph-Ph-OC.sub.6 H.sub.13                                                             8                                                 C.sub.6 H.sub.13 O-Ph-OCO-Np-OC.sub.9 H.sub.19                                                            4                                                 C.sub.3 H.sub.7 -Cy-COO-Ph-Pyl-C.sub.11 H.sub.23                                                          6                                                 C.sub.8 H.sub.17 -Cy-COO-Ph-Pyl-C.sub.11 H.sub.23                                                         2                                                 C.sub.5 H.sub.11 -Cy-COO-Ph-Pyl-C.sub.11 H.sub.23                                                         8                                                 C.sub.10 H.sub.21 O-Ph-COO-Ph-OCH.sub.2 *CH(CH.sub.3)C.sub.2 H.sub.5                                      15                                                C.sub.4 H.sub.9 -CH.sub.2 O-Ph-Pyl-C.sub.6 H.sub.13                                                       7                                                 C.sub.5 H.sub.11 -Cy-CH.sub.2 O-Ph-Pyl-C.sub.6 H.sub.13                                                   7                                                 C.sub.9 H.sub.19 O-Ph-OCH.sub.2 -Ph-Ph-C.sub.7 H.sub.15                                                   4                                                 C.sub.6 H.sub.13 *CH(CH.sub.3)O-Ph-COO-Ph-Ph-OCO*CH(CH.sub.3)OC.sub.4         H.sub.9                     2                                                 C.sub.12 H.sub.25 -Py2-Ph-OCO*CH(Cl)*CH(CH.sub.3)C.sub.2 H.sub.5                                          2                                                 ______________________________________                                    

Furthermore, the following example compounds were mixed to the liquidcrystal composition L with the following parts by weight so that liquidcrystal composition M was prepared.

    ______________________________________                                        Example                                                                       Compound                        Parts by                                      No.      Constitutional Formula Weight                                        ______________________________________                                        23       C.sub.6 H.sub.13 -Cy-CH═CH-Ph-(CH.sub.2).sub.2 L1-C.sub.10                H.sub.21               2                                             48       C.sub.5 H.sub.11 -Id1-Ph2F-(CH.sub.2).sub.2 -L1-C.sub.6 H.sub.13                                     2                                             88       C.sub.8 H.sub.17 OCH.sub.2 CH.sub.2 -Ph-Np-(CH.sub.2).sub.2                   -L1-C.sub.5 H.sub.11   2                                                      L                      94                                            ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition M being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            451 μsec 230 μsec                                                                            129 μsec                                  ______________________________________                                    

Comparative Example 2

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition L being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The results were asfollows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            784 μsec 373 μsec                                                                            197 μsec                                  ______________________________________                                    

EXAMPLE 37

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 36 so that liquid crystal composition N wasprepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                            Parts by Weight                                   ______________________________________                                        11      C.sub.10 H.sub.21 -Pr2-Ph-(CH.sub.2).sub.2 -L1-C.sub.4 H.sub.9                                    2                                                 43      C.sub.6 H.sub.13 -Cml-Ph-(CH.sub.2).sub.2 -L1-C.sub.8 H.sub.17                                    2                                                 92      C.sub.6 H.sub.13 -Ph-Ep1-(CH.sub.2).sub.2 -L1-C.sub.6 H.sub.13                                    2                                                         L                   94                                                ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition N being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            431 μsec 215 μsec                                                                            119 μsec                                  ______________________________________                                    

EXAMPLE 38

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 36 so that liquid crystal composition O wasprepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                        31      C.sub.9 H.sub.19 O-Tz2-Ph-(CH.sub.2).sub.2 -L1-C.sub.5 H.sub.11                                    2                                                58      C.sub.3 H.sub.7 -Py2-Ph-Ph-(CH.sub.2).sub.2 -L1-C.sub.8 H.sub.17                                   2                                                78      C.sub.4 H.sub.9 -Ph-CH.sub.2 O-Cy-(CH.sub.2).sub.2 -L1-C.sub.7                H.sub.15             1                                                        L                    95                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition O being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            510 μsec 263 μsec                                                                            150 μsec                                  ______________________________________                                    

EXAMPLE 39

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 36 so that liquid crystal composition P wasprepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.      Constitutional Formula                                                                           Parts by Weight                                   ______________________________________                                        331      C.sub.6 H.sub.13 O-Py2-Ph-(CH.sub.2).sub.4 -L2-C.sub.8 H.sub.17                                  2                                                 374      C.sub.5 H.sub.11 -Ha2-Ph-(CH.sub.2).sub.5 -L2-C.sub.11 H.sub.23                                  2                                                 407      C.sub.6 H.sub.13 -Ph-Ep1-(CH.sub.2).sub.4 -L2-C.sub.6 H.sub.13                                   2                                                          L                  94                                                ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition P being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            486 μsec 253 μsec                                                                            145 μsec                                  ______________________________________                                    

EXAMPLE 40

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 36 so that liquid crystal composition Q wasprepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                        310     C.sub.10 H.sub.21 -Py2-Ph-(CH.sub.2).sub.2 -LM1-C.sub.7 H.sub.15                                   1                                                456     C.sub.6 F.sub.13 CH.sub.2 O-Py2-Ph-(CH.sub.2).sub.2 -L1-C.sub.6               H.sub.13             2                                                483     C.sub.10 H.sub.21 O-Py2-Ph-(CH.sub.2).sub.2 -L1-C.sub.6 H.sub.13                                   2                                                        L                    95                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition Q being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            440 μsec 224 μsec                                                                            128 μsec                                  ______________________________________                                    

EXAMPLE 41

The following compounds were mixed with the following parts by weight sothat liquid crystal composition R was prepared.

    ______________________________________                                        Constitutinoal Formula Parts by Weight                                        ______________________________________                                        C.sub.8 H.sub.17 -Py2-Ph-OC.sub.6 H.sub.13                                                           10                                                     C.sub.8 H.sub.17 -Py2-Ph-OC.sub.9 H.sub.19                                                           5                                                      C.sub.10 H.sub.21 -Py2-Ph-OCOC.sub.8 H.sub.17                                                        7                                                      C.sub.10 H.sub.21 -Py2-Ph-O(CH.sub.2).sub.3 CH(CH.sub.3)OC.sub.3 H.sub.7                             7                                                      C.sub.12 H.sub.25 -Py2-Ph-O(CH.sub.2).sub.4 CH(CH.sub.3)OCH.sub.3                                    6                                                      C.sub.5 H.sub.11 -Py2-Ph-Ph-C.sub.6 H.sub.15                                                         5                                                      C.sub.7 H.sub.15 -Py2-Ph-Ph-C.sub.6 H.sub.13                                                         5                                                      C.sub.4 H.sub.9 -Cy-COO-Ph-Py1-C.sub.12 H.sub.25                                                     8                                                      C.sub.3 H.sub.7 -Cy-COO-Ph-Py1-C.sub.10 H.sub.21                                                     8                                                      C.sub.9 H.sub.19 O-Ph-COO-Ph-OC.sub.5 H.sub.11                                                       20                                                     C.sub.8 H.sub.17 -Ph-COO-Ph-Ph-OCH.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                 5                                                      C.sub.8 H.sub.17 -Ph-OCO-Ph-Ph-*CH(CH.sub.3)OCOC.sub.6 H.sub.13                                      5                                                      C.sub.6 H.sub.13 -Ph-OCH.sub.2 -Ph-Ph-C.sub.7 H.sub.15                                               6                                                      C.sub.12 H.sub.25 -Py2-Ph-OCH.sub.2 *CH(F)C.sub.6 H.sub.13                                           3                                                      ______________________________________                                    

The following example compounds were mixed with the following parts byweight to the foregoing liquid crystal composition R so that liquidcrystal composition S was prepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                            Parts by Weight                                   ______________________________________                                         1      C.sub.6 H.sub.13 -Ph-(CH.sub.2).sub.2 -L1-C.sub.8 H.sub.17                                        2                                                 25      C.sub.5 H.sub.11 -Pa-Ph-(CH.sub.2).sub.2 -L1-C.sub.8 H.sub.17                                     2                                                 34      C.sub.6 H.sub.13 -Boa2-Ph-(CH.sub.2).sub.2 -L1-C.sub.10 H.sub.21                                  2                                                         L                   94                                                ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition S being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            372 μsec 195 μsec                                                                            106 μsec                                  ______________________________________                                    

Comparative Example 3

A liquid crystal device was manufactured by the same method as thataccording to Example 26 except liquid crystal composition R mixed in thecomposition according to Example 24 being injected into the cell. Theoptical response speed was measured by the same method as that accordingto Example 31. The results were as follows.

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            653 μsec 317 μsec                                                                            159 μsec                                  ______________________________________                                    

EXAMPLE 42

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 41 so that liquid crystal composition T wasprepared.

    ______________________________________                                        Example                         Parts                                         Compound                        by                                            No.     Constitutional Formula  Weight                                        ______________________________________                                        26      C.sub.10 H.sub.21 -Pd-Ph-(CH.sub.2).sub.2 -L1-C.sub.6 H.sub.13                                        2                                             37      C.sub.6 H.sub.13 -Btb2-Ph-(CH.sub.2).sub.2 -L1-C.sub.14 H.sub.29                                      2                                             53      CH.sub.2 ═CH(CH.sub.2).sub.3 O-Ep2-Ph-(CH.sub.2).sub.2                    -L1-C.sub.6 H.sub.13    1                                                     R                       95                                            ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition T being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                  10° C.                                                                           25° C.                                                                          40° C.                                    ______________________________________                                        Response Speed                                                                            411 μsec 217 μsec                                                                            118 μsec                                  ______________________________________                                    

EXAMPLE 43

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 41 so that liquid crystal composition U wasprepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                        18      C.sub.5 H.sub.11 -Py2-Ph23F-(CH.sub.2).sub.2 -L1-C.sub.4 H.sub.9                                   2                                                72      C.sub.6 H.sub.13 -Ph-Py1-(CH.sub.2).sub.2 -L1-C.sub.6 H.sub.13                                     2                                                93      C.sub.9 H.sub.19 O-Gp1-(CH.sub.2).sub.2 -L1-C.sub.8 H.sub.17                                       2                                                        R                    94                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition U being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                    10° C.                                                                             25° C.                                                                          40° C.                                ______________________________________                                        Response Speed                                                                            366 μsec 191 μsec                                                                            104 μsec                                  ______________________________________                                    

EXAMPLE 44

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 41 so that liquid crystal composition V wasprepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.      Constitutional Formula                                                                          Parts by Weight                                    ______________________________________                                        153      C.sub.6 H.sub.13 -Tn-Ph-(CH.sub.2).sub.4 -L1-C.sub.7 H.sub.15                                   2                                                  170      H-Hb2-Ph-(CH.sub.2).sub.8 -L1-C.sub.8 H.sub.17                                                  1                                                  194      C.sub.5 H.sub.11 -Epl-(CH.sub.2).sub.8 -L1-C.sub.4 H.sub.9                                      2                                                           R                 95                                                 ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition V being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                    10° C.                                                                             25° C.                                                                          40° C.                                ______________________________________                                        Response Speed                                                                            450 μsec 237 μsec                                                                            130 μsec                                  ______________________________________                                    

EXAMPLE 45

The following example compounds were mixed with the following parts byweight in place of the example compounds mixed in the compositionaccording to Example 40 so that liquid crystal composition W wasprepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                        230     C.sub.8 H.sub.17 -Py2-Ph3F-(CH.sub.2).sub.2 -L1-Ph-C.sub.6                    H.sub.13             2                                                336     C.sub.6 H.sub.13 -Cy-Ph-(CH.sub.2).sub.8 -L2-C.sub.3 H.sub.6                  OC.sub.4 H.sub.9     2                                                379     C.sub.7 H.sub.15 -Ph-Py2-Ph-(CH.sub.2).sub.6 -L2-C.sub.10                     H.sub.21             2                                                        R                    94                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 26 except liquid crystal composition W being injected into thecell. The optical response speed was measured by the same method as thatof Example 31, and the switching state was observed. The uniformity oforientation in the liquid crystal device was excellent such thatmonodomain state was obtained. The results were as follows;

    ______________________________________                                                    10° C.                                                                             25° C.                                                                          40° C.                                ______________________________________                                        Response Speed                                                                            400 μsec 212 μsec                                                                            116 μsec                                  ______________________________________                                    

As can be understood from Examples 31 to 45, the liquid crystal deviceshaving the liquid crystal compositions G to K, M to Q and S to Waccording to the present invention between substrates thereof are ableto improve the operation characteristic and high speed response at lowtemperatures. Also the temperature dependency of the optical responsespeed can be reduced.

EXAMPLE 46

A liquid crystal device was manufactured by the same method as that ofExample 26 except that 2% water solution of polyvinyl alcohol resin(PUA-117 manufactured by Kurare) in place of dimethylacetoamide solutioncontaining polyimide resin precursor by 1.5% according to Example 26.The optical response speed was measured by the same method as thataccording to Example 31. The results were as follows:

    ______________________________________                                                    10° C.                                                                             25° C.                                                                          40° C.                                ______________________________________                                        Response Speed                                                                            378 μsec 202 μsec                                                                            109 μsec                                  ______________________________________                                    

EXAMPLE 47

A liquid crystal device was manufactured by the same method as that ofExample 26 except that the orientation control layer was formed only bypolyimide resin in such a manner that SiO2 according to Example 26 wasnot used. The optical response speed was measured by the same method asthat according to Example 31. The results were as follows:

    ______________________________________                                                    10° C.                                                                             25° C.                                                                          40° C.                                ______________________________________                                        Response Speed                                                                            350 μsec 188 μsec                                                                            101 μsec                                  ______________________________________                                    

As can be understood from Examples 46 and 47, the liquid crystal devicesrespectively having the liquid crystal compositions according to thepresent invention are able to improve the operation characteristic andthe temperature dependency of the optical response speed can be reducedeven if the structure of the device, such as the orientation controlfilm, is changed.

EXAMPLE 48

The following compounds were mixed with the following parts by weight sothat liquid crystal composition X was prepared.

    ______________________________________                                        C.sub.6 H.sub.13 -Py2-Ph-O (CH.sub.2).sub.4 C.sub.3 F.sub.7                                            5                                                    C.sub.11 H.sub.23 -Py2-Ph-OCH.sub.2 C.sub.4 F.sub.9                                                    10                                                   C.sub.8 H.sub.17 O-Pr1-Ph-O (CH.sub.2).sub.5 CH (CH.sub.3) C.sub.2            H.sub.5                  5                                                    C.sub.10 H.sub.21 -Py2-Ph-O (CH.sub.2).sub.4 CH (CH.sub.3)                                             10H.sub.3                                            C.sub.6 H.sub.13 -Py2-Ph-Ph-C.sub.8 H.sub.17                                                           7                                                    C.sub.8 H.sub.17 -Py2-Ph-OC.sub.6 H.sub.13                                                             15                                                   C.sub.8 H.sub.11 -Cy-COO-Ph-Py1-C.sub.12 H.sub.25                                                      5                                                    C.sub.4 H.sub.9 -Cy-COO-Ph-Py1-C.sub.11 H.sub.23                                                       5                                                    C.sub.3 H.sub.7 -Cy-COO-Ph-Py1-C.sub.11 H.sub.23                                                       5                                                    C.sub.12 H.sub.25 O-Ph-Pa-CO (CH.sub.2).sub.3 *CH (CH.sub.3) C.sub.2          H.sub.5                  2                                                    C.sub.10 H.sub.21 -Py2-Ph-OCH.sub.2 *CH (F) C.sub.2 H.sub.5                                            5                                                    C.sub.6 H.sub.13 -Cy-COO-Ph-OCH.sub.2 *CH (F) C.sub.6 H.sub.13                                         2                                                    C.sub.8 H.sub.17 -Ph-OCO-Ph-Ph-CH (CH.sub.3) OCOC.sub.6 H.sub.13                                       6                                                    C.sub.8 H.sub.17 -Py2-Ph-OCO-Ph-F                                                                      2                                                    C.sub.7 H.sub.15 O-Ph-Tz1-Ph-C.sub.5 H.sub.11                                                          3                                                    C.sub.6 H.sub.13 O-Btb2-Ph-OCO (CH.sub.2).sub.6 C.sub.2 F.sub.5                                        3                                                    C.sub.8 H.sub.17 O-Ph-COS-Ph-OCH.sub.2 C.sub.3 F.sub.7                                                 10                                                   ______________________________________                                    

Furthermore, the following example compounds were mixed with theforegoing liquid crystal composition X with the following parts byweight so that liquid crystal composition XA was prepared.

    ______________________________________                                        Example                                                                       Com-                                                                          pound                          Parts                                          No.     Constitutional Formula by Weight                                      ______________________________________                                        27      C.sub.6 H.sub.13 -Dt2-Ph-(CH.sub.2).sub.2 -L1-(CH.sub.2).sub.7                CH═CH.sub.2        1                                              33      C.sub.10 H.sub.21 -Dx2-Ph-(CH.sub.2).sub.2 -L1-C.sub.7 H.sub.15                                      1                                              104     C.sub.7 H.sub.15 -Tn-Ph-Py1-(CH.sub.2).sub.2 L1-C.sub.8 H.sub.17                                     1                                                      X                      97                                             ______________________________________                                    

Then, the foregoing liquid crystal compositions were used in thefollowing procedure to manufacture cells, the optical response of whichwas observed.

Two glass plates each having a thickness of 0.7 mm were prepared, and anITO film was formed on the glass plate so that an electrode, to whichvoltage was applied, was formed. Then, SiO₂ was evaporated on the ITOfilm so that an insulating layer was formed. Then, isopropyl alcoholsolution containing silane coupling material (KBM-602 manufactured byShinetsu Kagaku) by 0.2% was applied for 15 seconds by a spinnerrotating at a rotational speed of 2000 rpm so that surface treatment wasperformed. Then, heating and drying were performed at 120° C. for 20minutes. Furthermore, the glass plates with the ITO films, furthersubjected to surface treatment, were, for 15 seconds, applied withdimethyl acetoamide solution containing polyimide resin precursor(SP-510 manufactured by Toray) by 1.0% by a spinner rotating at arotational speed of 3000 rpm. After a desired film had been formed, heatshrinkage baking process was performed at 300° C. for 60 minutes. Thus,a film having a thickness of about 120 Å was applied.

The baked film was subjected to a rubbing process using acetate filling,and then it was cleaned with isopropyl alcohol solution. Then, silicabeads having an average diameter of 1.5 μm were placed on one of theglass plates in such a manner that the axes of the rubbing processes runparallel to one another. Then, an adhesive sealant ("LiqussoBond"manufactured by Chisso) was used to bond the glass plates to each other.Then, the glass plates were heated to 100° C. for 60 minutes so that acell was manufactured. The thickness of the cell was measured by a Berekphase plate, resulting in about 1.5 μm. Then, the liquid crystalcomposition XA was, in an isotropic fluid state, injected into the cell.Then, the cell was gradually cooled from the anisotropic phase to 25° C.at a rate of 20° C./hour so that a liquid crystal device (ferroelectricliquid crystal device) was manufactured. The liquid crystal device wasused to measure the contrast at 30° C. with the operating waveform (1/3bias ratio) shown in FIG. 5, resulting in 15.1.

Comparative Example 4

A liquid crystal device was manufactured by the same method as that ofExample 33 except liquid crystal composition X mixed in Example 33 beinginjected into the cell. By using similar operation waveforms, thecontrast at the time of the operation at 30° C. was measured. Theresulted contrast was 8.1.

EXAMPLE 49

The following example compounds were mixed with the foregoing with thefollowing parts by weight in place of the example compounds of thecompositions according to Example 48 so that liquid crystal compositionXB was prepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                        21      C.sub.6 H.sub.13 -Cy-Ph-(CH.sub.2).sub.2 -L1-C.sub.4 H.sub.8                  OC.sub.4 H.sub.9     1                                                36      C.sub.16 H.sub.33 O-Bta2-Ph-(CH.sub.2).sub.2 -L1-C.sub.6 H.sub.13                                  2                                                65      C.sub.4 H.sub.9 -Ph3TF-Pa-Ph-(CH.sub.2).sub.2 -L1-                                                 2                                                        (CH.sub.2).sub.3 CH(CH.sub.3).sub.2                                           X                    95                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 48 except the foregoing composition being used. By using similaroperation waveforms to those in Example 48, the contrast at the time ofthe operation at 30° C. was measured. The resulted contrast was 17.3.

EXAMPLE 50

The following example compounds were mixed with the foregoing with thefollowing parts by weight in place of the example compounds of thecompositions according to Example 48 so that liquid crystal compositionXC was prepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.      Constitutional Formula                                                                            Parts by Weight                                  ______________________________________                                        44       C.sub.8 H.sub.17 -1o1-Ph-(CH.sub.2).sub.2 -L1-C.sub.6 H.sub.13                                    1                                                86       C.sub.6 H.sub.13 -Ph2F-Td-(CH.sub.2).sub.2 -L1-                                                   2                                                         (CH.sub.2).sub.3 CH(CH.sub.3)C.sub.6 H.sub.13                        102      C.sub.5 H.sub.11 -Ph-Ph3F-Tz1-(CH.sub.2).sub.2 -L1-C.sub.3                    H.sub.7             2                                                         X                   95                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 48 except the foregoing composition being used. By using similaroperation waveforms to those in Example 48, the contrast at the time ofthe operation at 30° C. was measured. The resulted contrast was 17.7.

EXAMPLE 51

The following example compounds were mixed with the foregoing with thefollowing parts by weight in place of the example compounds of thecompositions according to Example 48 so that liquid crystal compositionXD was prepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                        6       C.sub.7 H.sub.15 O-Ph-Ph23F-(CH.sub.2).sub.2 -L1-C.sub.6 H.sub.13                                  1                                                59      C.sub.5 H.sub.11 -Ha2-Ph-(CH.sub.2).sub.2 -L1-C.sub.11 H.sub.23                                    2                                                95      C.sub.3 H.sub.7 COO-Ph-Gp1-(CH.sub.2).sub.2 -L1-C.sub.11 H.sub.23                                  2                                                        X                    95                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 48 except the foregoing composition being used. By using similaroperation waveforms to those in Example 48, the contrast at the time ofthe operation at 30° C. was measured The resulted contrast was 21.2.

EXAMPLE 52

The following example compounds were mixed with the foregoing with thefollowing parts by weight in place of the example compounds of thecompositions according to Example 48 so that liquid crystal compositionXE was prepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                        126     C.sub.8 H.sub.17 -Py2-Ph-(CH.sub.2).sub.4 -L1-CH.sub.2 OC.sub.6               H.sub.13             2                                                147     C.sub.6 H.sub.13 -Cm1-Ph-(CH.sub.2).sub.4 -L1-C.sub.8 H.sub.17                                     1                                                186     C.sub.3 H.sub.7 -Ph2C1-Tn-(CH.sub.2).sub.13 -L1-C.sub.10 H.sub.21                                  1                                                        X                    96                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 48 except the foregoing composition being used. By using similaroperation waveforms to those in Example 48, the contrast at the time ofthe operation at 30° C. was measured. The resulted contrast was 19.0.

EXAMPLE 53

The following example compounds were mixed with the foregoing with thefollowing parts by weight in place of the example compounds of thecompositions according to Example 48 so that liquid crystal compositionXF was prepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                        226     C.sub.6 H.sub.13 O-Py2-Ph-(CH.sub.2).sub.6 -L2-Ph-C.sub.6                     H.sub.13             2                                                261     C.sub.12 H.sub.25 -Btb2-Ph-(CH.sub.2).sub.9 -L1-Ph-H                                               2                                                294     C.sub.8 H.sub.17 -Ph-Tz1-(CH.sub.2).sub.2 -L1-Ph-H                                                 1                                                        X                    95                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 33 except the foregoing composition being used. By using similaroperation waveforms to those in Example 48, the contrast at the time ofthe operation at 30° C. was measured. The resulted contrast was 18.2.

EXAMPLE 54

The following example compounds were mixed with the foregoing with thefollowing parts by weight in place of the example compounds of thecompositions according to Example 48 so that liquid crystal compositionXG was prepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.     Constitutional Formula                                                                             Parts by Weight                                  ______________________________________                                        326     C.sub.10 H.sub.21 -Pr2-Ph-(CH.sub.2).sub.6 -L2-C.sub.4 H.sub.9                                     2                                                460     C.sub.10 F.sub.21 CH.sub.2 O-Py2-Ph-(CH.sub.2).sub.2 -L1.-C.sub.6             H.sub.13             2                                                464     C.sub.6 F.sub.13 CH.sub.2 O-Ph-Ph-(CH.sub.2).sub.8 -L2-C.sub.6                H.sub.13             1                                                        X                    95                                               ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 48 except the foregoing composition being used. By using similaroperation waveforms to those in Example 48, the contrast at the time ofthe operation at 30° C. was measured. The resulted contrast was 23.1.

As can be understood from Examples 48 to 54, the liquid crystal deviceincluding any of the liquid crystal compositions XA, XB, XC, XD, XE, XFand XG had intense contrast at the time of the operation.

EXAMPLE 55

The following example compounds were mixed with the foregoing with thefollowing parts by weight in place of the example compounds of thecompositions according to Example 48 so that liquid crystal compositionXH was prepared.

    ______________________________________                                        Example                                                                       Compound                                                                      No.      Constitutional Formula                                                                           Parts by Weight                                   ______________________________________                                        19       C.sub.10 H.sub.21 -Py2-Ph-(CH.sub.1).sub.2 -L1-C.sub.6 H.sub.13                                  5                                                          X                  95                                                ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 48 except the foregoing composition being used. By using similaroperation waveforms to those in Example 48, the contrast at the time ofthe operation at 30° C. was measured. The resulted contrast was 16.3.

Comparative Example 5

Compounds which had been disclosed in U.S. Pat. No. 4,973,425 and inwhich a lactone ring and a mesogen skeleton were bonded with each by amethyleneoxy group was prepared by a method disclosed in the same. Themelting points of compounds A and B are as follows:

    ______________________________________                                                                        melting                                                                       point                                         ______________________________________                                        Comparative                                                                              cis-C.sub.10 H.sub.21 -Py2-Ph-OCH.sub.2 -L2-C.sub.6 H.sub.13                                       137.3° C.                              Compound A                                                                    Comparative                                                                              trans-C.sub.10 H.sub.21 -Py2-Ph-OCH.sub.2 -L2-C.sub.6 H.sub.13                                      97.1° C.                              Compound B                                                                    ______________________________________                                    

Then, compound A was mixed with the following parts by weight in placeof the example compound of the composition according to Example 48 sothat liquid crystal composition XI as prepared.

    ______________________________________                                        Constitutional Formula                                                                            Parts by Weight                                           ______________________________________                                        cis-C.sub.10 H.sub.21 -Py2-Ph-OCH.sub.2 -L2-C.sub.6 H.sub.13                                      5                                                         X                   95                                                        ______________________________________                                    

A liquid crystal device was manufactured by the same method as that ofExample 48 except the foregoing composition being used. By using similaroperation waveforms to those in Example 48, the contrast at the time ofthe operation at 30° C. was measured. The resulted contrast was 10.4.

Compound B was mixed with the following parts by weight in place of theexample compound of the composition according to Example 48 so thatliquid crystal composition XJ was prepared.

    ______________________________________                                        Constitutional Formula                                                                             Parts by Weight                                          ______________________________________                                        trans-C.sub.10 H.sub.21 -Py2-Ph-OCH.sub.2 -L2-C.sub.6 H.sub.13                                     5                                                        X                    95                                                       ______________________________________                                    

A ferroelectric liquid crystal device was manufactured by the samemethod as that of Example 48 except the foregoing composition beingused. By using similar operation waveforms to those in Example 48, thecontrast at the time of the operation at 30° C. was measured. Theresulted contrast was 9.2.

As can be understood from Example 55 and Comparative Example 5, theliquid crystal device containing liquid crystal composition H accordingto the present invention exhibited greatly intense contrast at the timeof the operation as compared with the liquid crystal device containingliquid crystal composition XI and XJ including compound A or B.

EXAMPLE 56

A liquid crystal device was manufactured by the same method as that ofExample 48 except 2% water solution of polyvinyl alcohol resin (PVA-117manufactured by Kurare) being used in place of dimethylacetoamidesolution of polyimide resin precursor by 1.0% according to Example 48.By employing a similar method to that in Example 48, the contrast at thetime of the operation at 30° C. was measured. The resulted contrast was16.1.

EXAMPLE 57

A liquid crystal device was manufactured by the same method as that ofExample 48 except the orientation control layer being formed by onlypolyimide resin without SiO2 employed in Example 48. By employing asimilar method to that in Example 48, the contrast at the time of theoperation at 30° C. was measured. The resulted contrast was 14.5.

EXAMPLE 58

A ferroelectric liquid crystal device was manufactured by the samemethod as that of Example 48 except 1% NMP solution of polyamide acid(LQ1802 manufactured by Hitachi Kasei) being baked at 270° C. for onehour in place of dimethyl acetoamide solution of polyimide precursor by1.0% employed in Example 48. By employing a similar method to that inExample 48, the contrast at the time of the operation at 30° C. wasmeasured. The resulted contrast was 28.1.

As can be understood from Examples 56, 57 and 58, even if the structureof the device is changed, the liquid crystal device according to thepresent invention having the liquid crystal composition disposed betweensubstrates enables intense contrast similar to the device according toExample 48. Even if the operation waveform is changed, the detailedinvestigation resulted in that the liquid crystal device having theliquid crystal composition (ferroelectric liquid crystal composition)according to the present invention enables intense contrast to beobtained.

As described above, according to the present invention, there isprovided a novel optically active compound exhibiting excellentperformance of realizing spontaneous polarization. In particular, theliquid crystal composition containing the optically active compoundaccording to the present invention can be operated by making using ofthe ferroelectric characteristic of the liquid crystal composition. Asdescribed above, the liquid crystal device according to the presentinvention using the characteristic of the liquid crystal composition hasexcellent switching characteristic, high-speed response, capability ofreducing in dependency of the optical response speed upon thetemperature, and intense contrast. A display apparatus comprising theliquid crystal device according to the present invention with a lightsource, an operating circuit and the like as a display device is anexcellent apparatus.

Although the invention has been described in its preferred form with acertain degree of particularity, it is understood that the presentdisclosure of the preferred form can be changed in the details ofconstruction and the combination and arrangement of parts may beresorted to without departing from the spirit and the scope of theinvention as hereinafter claimed.

What is claimed is:
 1. An optically active compound represented by thefollowing general formula (I):

    R.sub.1 --A.sub.1 --A.sub.2 --X.sub.1 --A.sub.3 --(CH.sub.2).sub.p --L--A.sub.4 --R.sub.2                                    (I)

where R₁ is F, CN or straight chain, branched alkyl group (one or more--CH₂ -- in the alkyl group may be replaced by --O--, --S--, --CO--,--CH(CN)--, --CH═CH-- or --C.tbd.C-- under condition that heteroatoms donot position adjacently and one or more hydrogen atom in the alkyl groupmay be replaced by fluorine atom) having 1 to 30 carbon atoms or cyclicalkyl group wherein the cyclic alkyl is a 3-6 membered heterocyclic ringhaving 1 or 2 oxygen heteroatoms, wherein 1 or 2 nonadjacent --CH₂ --moieties is optionally replaced with --CO--, said heterocyclic ringbeing optionally substituted by at least one alkyl group and R₂ is H, F,CN or straight chain or branched alkyl group (one or more --CH₂ -- inthe alkyl group may be replaced by --O--, --S--, --CO--, --CH(CN)--,--CH═CH-- or --C.tbd.C-- under condition that heteroatoms do notposition adjacently and one or more hydrogen atom in the alkyl group maybe replaced by fluorine atom) having 1 to 30 carbon atoms; A₃ is a groupselected from the group consisting of 1,4-phenylene, pyridine-2,5-diyl,pyrimidine-2,5-diyl, pyrazine-2,5-diyl, pyridazine-3,6-diyl,1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-ditiane-2,5-diyl,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,benzoxazole-2,5-diyl, benzoxazole-2,6-diyl, benzothiazole-2,5-diyl,benzothiazole-2,6-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl, 2,6-naphthylene,indane-2,5-diyl, 2-alkylindane-2,5-diyl (the alkyl group is a straightchain or branched alkyl group having 1 to 18 carbon atoms),indanone-2,6-diyl, 2-alkylindane-2,6-diyl (the alkyl group is a straightchain or branched alkyl group having 1 to 18 carbon atoms),coumarane-2,5-diyl and 2-alkylcoumarane-2,5-diyl (the alkyl group is astraight chain or branched alkyl group having 1 to 18 carbon atoms),each of which may be substituted by at least one substituent selectedfrom the group consisting of F, Cl, Br, CH₃, and CN; A₁, A₂ and A₄ areindependently single bonds or A₃ ; X₁ ⁺ is a single bond, --COO--,--OCO--, --CH₂ O--, --OCH₂ --, --CH₂ CH₂ --, --CH═CH-- or --C.tbd.C--; pis an integer from 2 to 20; L is optically active butanolyde-2,4-diyl oroptically active 4-alkylbutanolyde-2,4-diyl (the alkyl group isstraight-chain or branched alkyl group having 1 to 5 carbon atoms) oroptically active 2-alkylbutanolyde-2,4-diyl (the alkyl group isstraight-chain or branched alkyl group having 1 to 5 carbon atoms). 2.An optically active compound according to claim 1, wherein saidoptically active compound represented by general formula (I) is any ofcompounds in (Ia) to (Id):(Ia) an optically active compound in which A₁and A₂ respectively are single bonds or groups selected from the groupconsisting of 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl,pyrazine-2,5-diyl, pyridazine-3,6-diyl, 1,4-cyclohexylene,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,benzoxazole-2,5-diyl, benzoxazole-2,6-diyl, benzothiazole-2,5-diyl,benzothiazole-2,6-diyl, benzofuran-2,5-diyl, benzofuran-2-6-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl, 2,6-naphthylene,indane-2,5-diyl and coumarane-2,5-diyl, each of which may be substitutedby at least one substituent selected from the group consisting of F, Cl,Br, CH₃, CF₃ and CN, A₃ is 1,4-phenylene, which may be substituted by atleast one substituent selected from the group consisting of F, Cl, Br,CH₃, CF₃ and CN and A₄ is a single bond; (Ib) an optically activecompound in which A₁ and A₂ are single bonds or 1,4-phenylene, which maybe substituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN, A₃ is a group selected fromthe group consisting of pyridine-2,5-diyl, pyrimidine-2,5-diyl,pyrazine-2,5-diyl, pyridazine-3,6-diyl, 1,4-cyclohexylene,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,benzoxazole-2,5-diyl, benzoxazole-2,6-diyl, benzothiazole-2,5-diyl,benzothiazole-2,6-diyl, benzofuran-2,5-diyl, benzofuran-2-6-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl, 2,6-naphthylene,indane-2,5-diyl and coumarane-2,5-diyl and A₄ is a single bond; (Ic) anoptically active compound in which A₁ is a single bond, A₂ and A₄ arerespectively groups selected from the following group consisting of1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl,pyrazine-2,5-diyl, pyridazine-3,6-diyl, 1,4-cyclohexylene,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,benzoxazole-2,5-diyl, benzoxazole-2,6-diyl, benzothiazole-2,5-diyl,benzothiazole-2,6-diyl, benzofuran-2,5-diyl, benzofuran-2-6-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl, 2,6-naphthylene,indane-2,5-diyl and coumarane-2,5-diyl, each of which may be substitutedby at least one substituent selected from the group consisting of F, Cl,Br, CH₃, CF₃ and CN, and A₃ is 1,4-phenylene, which may be substitutedby at least one substituent selected from the group consisting of F, Cl,Br, CH₃, CF₃ and CN; and (Id) an optically active compound in which A₁is a single bond, A₂ is a single bond or 1,4-phenylene, which may besubstituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN, A₃ is a group selected fromthe group consisting of pyridine-2,5-diyl, pyrimidine-2,5-diyl,pyrazine-2,5-diyl, pyridazine-3,6-diyl, 1,4-cyclohexylene,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,benzoxazole-2,5-diyl, benzoxazole-2,6-diyl, benzothiazole-2,5-diyl,benzothiazole-2,6-diyl, benzofuran-2,5-diyl, benzofuran-2-6-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl, 2,6-naphthylene,indane-2,5-diyl and coumarane-2,5-diyl and A₄ is 1,4-phenylene, whichmay be substituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN.
 3. An optically activecompound according to claim 1, wherein said optically active compoundrepresented by general formula (I) is any of compounds in (Iaa) to(Idb):(Iaa) an optically active compound in which A₁, A₂, A₄ and X₁ aresingle bonds, and A₃ is 1,4-phenylene, which may be substituted by atleast one substituent selected from the group consisting of F, Cl, Br,CH₃, CF₃ and CN; (Iab) an optically active compound in which A₁, A₄ andX₁ are single bonds, A₂ is a group selected from the group consisting of1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl,1,4-cyclohexylene, thiophene-2,5-diyl, thiazole-2,5-diyl,thiaziazole-2,5-diyl, benzothiazole-2,6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene and indane-2,5-diyl, each of whichmay be substituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN, and A₃ is 1,4-phenylene orthat having one or two substituents, which may be substituted by atleast one substituent selected from the group consisting of F, Cl, Br,CH₃, CF₃ and CN; (Iac) an optically active compound in which A₄ and X₁are single bonds, A₁ is pyrimidine-2,5-diyl, A₂ and A₃ are1,4-phenylene, which may be substituted by at least one substituentselected from the group consisting of F, Cl, Br, CH₃, CF₃ and CN; (Iad)an optically active compound in which A₄ and X₁ are single bonds, A₁ andA₂ are respectively groups selected from the group consisting of1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl,1,4-cyclohexylene, thiophene-2,5-diyl, thiazole-2,5-diyl,thiaziazole-2,5-diyl and indane-2,5-diyl, each of which may besubstituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN, and A₃ is 1,4-phenylene, whichmay be substituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN; (Iba) an optically activecompound in which A₁, A₂, A₄ and X₁ are respectively single bonds, A₃ isa group selected from the group consisting of pyridine-2,5-diyl,1,4-cyclohexylene, quinoxaline-2,6-diyl, quinoline-2,6-diyl and2,6-naphthylene; (Ibb) an optically active compound in which A₁, A₄ andX₁ are single bonds, A₂ is 1,4-phenylene, which may be substituted by atleast one substituent selected from the group consisting of F, Cl, Br,CH₃, CF₃ and CN, and A₃ is a group selected from the group consisting ofpyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,4-cyclohexylene,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl and 2,6-naphthylene; (Ica) anoptically active compound in which A₁ and X₁ are single bonds, A₂ isgroups selected from the group consisting of 1,4-phenylene,pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,4-cyclohexylene,thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl,benzothiazole-2,6-diyl, quinoxaline-2,6-diyl, quinoline-2,6-diyl,2,6-naphthylene and indane-2,5-diyl, each of which may be substituted byat least one substituent selected from the group consisting of F, Cl,Br, CH₃, CF₃ and CN, and A₃ and A₄ are 1,4-phenylene, which may besubstituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN; (Ida) an optically activecompound in which A₁ and X₁ are single bonds, A₃ is a group selectedfrom the group consisting of pyridine-2,5-diyl, pyrimidine-2,5-diyl,1,4-cyclohexylene, thiophene-2,5-diyl, thiazole-2,5-diyl,thiaziazole-2,5-diyl, benzothiazole-2,6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene and indane-2,5-diyl, A₂ and A₄ are1,4-phenylene, which may be substituted by at least one substituentselected from the group consisting of F, Cl, Br, CH₃, CF₃ and CN; and(Idb) an optically active compound in which A₁, A₂ and X₁ are singlebonds, A₃ is a group selected from the group consisting of1,4-phenylene, pyridine-2,5-diyl, 1,4-cyclohexylene,quinoxaline-2,6-diyl, quinoline-2,6-diyl and 2,6-naphthylene, and A₄ is1,4-phenylene, which may be substituted by at least one substituentselected from the group consisting of F, Cl, Br, CH₃, CF₃ and CN.
 4. Anoptically active compound according to claim 1, wherein R₁ is selectedfrom the group consisting of: ##STR19## and R₂ is selected from thegroup consisting of: ##STR20## where a is an integer from 1 to 16; d, gand i are independently integers from 0 to 7; b, e, h, j and k areindependently integers from 1 to 10; f and w are independently 0 or 1;m, n, q, r, s and t are independently integers from 0 to 10 in whichb+d≦16, e+f+g≦16 and h+i≦16; E is CH₃ or CF₃ ; Y₁ is a single bond,--O--, --COO-- or --OCO--; Y₂ is --COO--, --CH₂ O, --CH₂ CH₂ O--, --CH₂CH₂ CH₂ O-- or --CH₂ CH₂ --; and Y₃ is a single bond, --COO--, CH₂ O--,--OCO-- or --OCH₂ -- which may be optically active groups.
 5. Anoptically active compound according to claim 1, wherein p of saidoptically active compound represented by general formula (I) is aninteger from 2 to
 12. 6. An optically active compound according to claim1, wherein p of said optically active compound represented by generalformula (I) is 2, 4, 6 or
 8. 7. An optically active compound accordingto claim 1 wherein p of said optically active compound represented bygeneral formula (I) is 3, 5, 7 or
 9. 8. An optically active compoundcomprising a structure represented by the following general formula(I'): ##STR21## where R₁ ' is H, F, CN or a straight, branched alkylgroup (one or more --CH₂ -- in the alkyl group may be replaced by --O--,--S--, --CO--, --CH(CN)--, --CH═CH-- or --C.tbd.C-- under condition thatheteroatoms do not position adjacent and the hydrogen atom in the alkylgroup may be replaced by a fluorine atom) or cyclic alkyl group whereinthe cyclic alkyl is a 3-6 membered heterocyclic ring having 1 or 2oxygen heteroatoms, wherein 1 or 2 non-adjacent --CH₂ -- moieties isoptionally replaced with --CO--, said heterocyclic ring being optionallysubstituted by at least one alkyl group having 1 to 20 carbon atoms; R₂' is a straight or branched alkyl group (one or more --CH₂ -- in thealkyl group may be replaced by --O--, --CO--, or --CH═CH-- undercondition that heteroatoms do not position adjacent and the hydrogenatom in the alkyl group may be replaced by a fluorine atom) having 1 to20 carbon atoms; A₃ ' is a group selected from the group consisting of1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl,pyrazine-2,5-diyl, pyridazine-3,6-diyl, 1,4-cyclohexylene,1,3-dioxane-2,5-diyl, 1,3-ditiane-2,5-diyl, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzoxazole-2,5-diyl,benzoxazole-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl,benzofuran-2,5-diyl, benzofuran-2,6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene, indane-2,5-diyl,2-alkylindane-2,5-diyl (the alkyl group is a straight chain or branchedalkyl group having 1 to 18 carbon atoms), indanone-2,6-diyl,2-alkylindane-2,6-diyl (the alkyl group is a straight chain or branchedalkyl group having 1 to 18 carbon atoms), coumarane-2,5-diyl and2-alkylcoumarane-2,5-diyl (the alkyl group is a straight chain orbranched alkyl group having 1 to 18 carbon atoms), each of which may besubstituted by at least one substituent selected from the groupconsisting of F, Cl, Br, CH₃, CF₃ and CN; A₁ ' and A₂ ' are single bondsor selected from A₃ '; X₁ ' is a single bond, --COO--, --OCO--, --CH₂O--, --OCH₂ --, --CH₂ CH₂ --, --CH═CH-- or --C.tbd.C--; and * representsoptically active characteristic.
 9. An optically active compoundaccording to claim 8, wherein said optically active compound representedby general formula (I') is any of materials in (Ia') or (Ib'):(Ia') anoptically active compound in which A₁ ' and A₂ ' are single bonds orgroups selected from the group consisting of 1,4-phenylene,pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyrazine-2,5-diyl,pyridazine-3,6-diyl, 1,4-cyclohexylene, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzoxazole-2,5-diyl,benzoxazole-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl,benzofuran-2,5-diyl, benzofuran-2-6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene, indane-2,5-diyl andcoumarane-2,5-diyl, each of which may be substituted by at least onesubstituent selected from the group consisting of F, Cl, Br, CH₃, CF₃and CN and A₃ is 1,4-phenylene substituted by at least one groupselected from the group consisting of F, Cl, Br, CH₃, CF₃ and CN and A₄is a single bond; or (Ib') an optically active compound in which A₁ 'and A₂ ' are single bonds or 1,4-phenylene, which may be substitutes byat least one substituent selected from the group consisting of F, Cl,Br, CH₃, CF₃ and CN, A₃ is a group selected from the group consisting ofpyridine-2,5-diyl, pyrimidine-2,5-diyl, pyrazine-2,5-diyl,pyridazine-3,6-diyl, 1,4-cyclohexylene, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzoxazole-2,5-diyl,benzoxazole-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl,benzofuran-2,5-diyl, benzofuran-2-6-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl, 2,6-naphthylene, indane-2,5-diyl andcoumarane-2,5-diyl.
 10. An optically active compound according to claim8, wherein said optically active compound represented by general formula(I') is any of materials in (Iaa') or (Ibb'):(Iaa') an optically activecompound in which A₁ ', A₂ ' and X₁ ' are single bonds and A₃ ' is1,4-phenylene, which may be substituted by at least one substituentselected from the group consisting of F, Cl, Br, CH₃, CF₃ and CN; (Iab')an optically active compound in which A₁ ' is a single bond and both A₂' and A₃ ' are 1,4-phenylene, which may be at least one substituentselected from the group consisting of F, Cl, Br, CH₃, CF₃ and CN; (Iac')an optically active compound in which A₁ ' and X₁ ' are single bonds, A₂' is a group selected from the group consisting of pyridine-2,5-diyl,pyrimidine-2,5-diyl, 1,4-cyclohexylene, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzothiazole-2,6-diyl,quinoxaline-2,6-diyl, quinoline-2,6-diyl, 2,6-naphthylene andindane-2,5-diyl, A₃ ' is 1,4-phenylene, which may be substituted by atleast one substituent selected from the group consisting of F, Cl, Br,CH₃, CF₃ and CN; and (Iba') an optically active compound in which A₁ ',A₂ ' and X₁ ' are single bonds and A₃ ' is a group selected from thegroup consisting of pyridine-2,5-diyl, 1,4-cyclohexylene,quinoxaline-2,6-diyl, quinoline-2,6-diyl and 2,6-naphthylene (Ibb') Anoptically active compound in which A₁ ' and X₁ ' are single bonds, A₂ 'is 1,4-phenylene, which may be substituted by at least one substituentselected from the group consisting of F, Cl, Br, CH₃, CF₃ and CN and A₃' is a group selected from the group consisting of pyridine-2,5-diyl,pyrimidine-2,5-diyl, 1,4-cyclohexylene, thiophene-2,5-diyl,thiazole-2,5-diyl, thiaziazole-2,5-diyl, quinoxaline-2,6-diyl,quinoline-2,6-diyl and 2,6-naphthylene.
 11. An optically active compoundaccording to claim 8, wherein R1' and R2' of said optically activecompound represented by general formula (I') respective are any ofmaterials in (i') to (v'): ##STR22## where a' is an integer from 1 to16, d', g' and i' respectively are integers from 0 to 7, b', e', h' andj' respectively are integers from 1 to 10, f' is 0 or 1 in whichb'+d'≦16, e'+f'+g'≦16 and h'+i'≦16 are satisfied, Y1' is a single bond,--O--, --COO-- or --OCO-- and Y₂ ' is --COO-- or --CH₂ O--, which may beoptically active.
 12. A liquid crystal composition comprising one ormore kinds of said optically active compounds claimed in any of claims1-11.
 13. A liquid crystal composition according to claim 12, whereinsaid optically active compound is contained by 1 wt % to 80 wt %.
 14. Aliquid crystal composition according to claim 12, wherein said opticallyactive compound is contained by 1 wt % to 60 wt %.
 15. A liquid crystalcomposition according to claim 12, wherein said optically activecompound is contained by 1 wt % to 40 wt %.
 16. A liquid crystalcomposition according to claim 12, wherein said liquid crystal compoundhas a chiral smectic phase.
 17. A liquid crystal composition accordingto claim 12, wherein two or more kinds of said optically activecompounds.
 18. A liquid crystal device comprising said liquid crystalcomposition according to claim 16 disposed between a pair of electrodesubstrates.
 19. A liquid crystal device according to claim 18, whereinan orientation control layer is further formed on said electrodesubstrate.
 20. A liquid crystal device according to claim 18, whereinsaid orientation control layer is a layer subjected to a rubbingprocess.
 21. A liquid crystal device according to claim 18, wherein saidpair of electrode substrates are disposed with a thickness realized whenspirals of liquid crystal molecules are untied.
 22. A liquid crystalapparatus comprising said liquid crystal device according to claim 18and a circuit for operating said liquid crystal device.
 23. A liquidcrystal apparatus according to claim 22, wherein said liquid crystaldevice is used as a display device.
 24. A liquid crystal apparatusaccording to claim 23 further comprising a light source.
 25. A displaymethod comprising the step of:selecting a liquid crystal deviceaccording to claim 22; and controlling said liquid crystal compositionto display information.